2-(4-fluorooxan-4-yl)-2-hydroxyacetonitrile

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 306A (11.5 g) was dissolved in dichloromethane (40 mL) in a polypropylene bottle. The bottle was cooled to 0° C. To this mixture was added 70% hydrogen fluoride-pyridine (10.31 mL) slowly. The mixture was allowed to warm to room temperature over 3 hours, and stirred for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used to neutralize the mixture carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each).The combined organic layers were washed with 1% HCl, brine, dried (MgSO4), filtered and concentrated to give the desired compound which was used directly in the next reaction. to warm to room temperature over 3 hours until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each).The combined organic layers were washed with 1% HCl, brine dried (MgSO4) filtered concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 306A (11.5 g) was dissolved in dichloromethane (40 mL) in a polypropylene bottle. The bottle was cooled to 0° C. To this mixture was added 70% hydrogen fluoride-pyridine (10.31 mL) slowly. The mixture was allowed to warm to room temperature over 3 hours, and stirred for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used to neutralize the mixture carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each).The combined organic layers were washed with 1% HCl, brine, dried (MgSO4), filtered and concentrated to give the desired compound which was used directly in the next reaction. to warm to room temperature over 3 hours until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each).The combined organic layers were washed with 1% HCl, brine dried (MgSO4) filtered concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 296A (11.5 g) was dissolved in dichloromethane (40 mL) in a polypropylene bottle. The bottle was cooled to 0° C. To this solution was added 70% hydrogen fluoride-pyridine (10.3 mL) slowly. The solution was allowed to warm to room temperature over 3 hours, and stirred for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used to neutralize the solution carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each). The combined organic layers were washed with 1% aqueous HCl, brine, dried (MgSO4), filtered and concentrated to give the desired compound which was used directly in the next reaction. to warm to room temperature over 3 hours until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each) The combined organic layers were washed with 1% aqueous HCl, brine dried (MgSO4) filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 37A (11.5 g) in dichloromethane (40 mL) in a polypropylene bottle was treated with 70% hydrogen fluoride-pyridine (10.4 mL) dropwise at 0° C. The solution was allowed to warm to room temperature over 3 hours, and stirred for an additional 1.5 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each). The combined organic layers were washed with 5% HCl (50 mL each, twice), brine, dried over MgSO4, filtered and concentrated to give the desired product which was used directly in the next step. until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each) The combined organic layers were washed with 5% HCl (50 mL each twice), brine, dried over MgSO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 37A (11.5 g) in dichloromethane (40 mL) in a polypropylene bottle was treated with 70% hydrogen fluoride-pyridine (10.4 mL) dropwise at 0° C. The solution was allowed to warm to room temperature over 3 hours, and stirred for an additional 1.5 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each). The combined organic layers were washed with 5% HCl (50 mL each, twice), brine, dried over MgSO4, filtered and concentrated to give the desired product which was used directly in the next step. until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each) The combined organic layers were washed with 5% HCl (50 mL each twice), brine, dried over MgSO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 37A (11.5 g) in dichloromethane (40 mL) in a polypropylene bottle was treated with 70% hydrogen fluoride-pyridine (10.4 mL) dropwise at 0° C. The solution was allowed to warm to room temperature over 3 hours, and stirred for an additional 1.5 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each). The combined organic layers were washed with 5% HCl (50 mL each, twice), brine, dried over MgSO4, filtered and concentrated to give the desired product which was used directly in the next step. until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each) The combined organic layers were washed with 5% HCl (50 mL each twice), brine, dried over MgSO4 filtered concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 306A (11.5 g) was dissolved in dichloromethane (40 mL) in a polypropylene bottle. The bottle was cooled to 0° C. To this mixture was added 70% hydrogen fluoride-pyridine (10.31 mL) slowly. The mixture was allowed to warm to room temperature over 3 hours, and stirred for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used to neutralize the mixture carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each). The combined organic layers were washed with 1% HCl, brine, dried (MgSO4), filtered and concentrated to give the desired compound which was used directly in the next reaction. to warm to room temperature over 3 hours until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each) The combined organic layers were washed with 1% HCl, brine dried (MgSO4) filtered concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 306A (11.5 g) was dissolved in dichloromethane (40 mL) in a polypropylene bottle. The bottle was cooled to 0° C. To this mixture was added 70% hydrogen fluoride-pyridine (10.31 mL) slowly. The mixture was allowed to warm to room temperature over 3 hours, and stirred for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used to neutralize the mixture carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each). The combined organic layers were washed with 1% HCl, brine, dried (MgSO4), filtered and concentrated to give the desired compound which was used directly in the next reaction. to warm to room temperature over 3 hours until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each) The combined organic layers were washed with 1% HCl, brine dried (MgSO4) filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 296A (11.5 g) was dissolved in dichloromethane (40 mL) in a polypropylene bottle. The bottle was cooled to 0*C. To this solution was added 70% hydrogen fluoride-pyridine (10.3 mL) slowly. The solution was allowed to warm to room temperature over 3 hours, and stirred for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used to neutralize the solution carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each). The combined organic layers were washed with 1% aqueous HCl, brine, dried (MgSO4), filtered and concentrated to give the desired compound which was used directly in the next reaction. The bottle was cooled to 0*C until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each) The combined organic layers were washed with 1% aqueous HCl, brine dried (MgSO4) filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: EXAMPLE 37A (11.5 g) in dichloromethane (40 mL) in a polypropylene bottle was treated with 70% hydrogen fluoride-pyridine (10.4 mL) dropwise at 0° C. The solution was allowed to warm to room temperature over 3 hours, and stirred for an additional 1.5 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and poured into saturated aqueous NaHCO3. Additional solid NaHCO3 was used carefully until bubbling ceased. The organic layer was isolated, and the aqueous layer was extracted with additional ethyl acetate three times (150 mL each). The combined organic layers were washed with 5% HCl (50 mL each, twice), brine, dried over MgSO4, filtered and concentrated to give the desired product which was used directly in the next step. until bubbling The organic layer was isolated the aqueous layer was extracted with additional ethyl acetate three times (150 mL each) The combined organic layers were washed with 5% HCl (50 mL each twice), brine, dried over MgSO4 filtered concentrated