ETHYL 4-HYDROXY-1-METHYLCYCLOHEXANECARBOXYLATE

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:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1-Allyl-4-hydroxy-cyclohexanecarboxylic acid ethyl ester was prepared by deprotecting Intermediate 98 using a method analogous to the method used to prepare Intermediate 67.

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

实验步骤: Ethyl 4-hydroxy-1-methylcyclohexanecarboxylate (Intermediate 67, 930 mg, 4.99 mmol), triphenylphosphine (3.143 g, 11.98 mmol), and phthalimide (882 mg, 5.99 mmol) were dissolved in 60 mL of THF. DIAD (2.33 mL, 11.98 mmol) was then added and the reaction mixture was stirred overnight at room temperature. The mixture was concentrated under vacuum, and the residue was chromatographed on silica gel using an ethyl acetate/heptane gradient. The title compound (1 g) was obtained as a clear oil. The mixture was concentrated under vacuum the residue was chromatographed on silica gel using an ethyl acetate/heptane gradient

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

实验步骤: Ethyl 4-(tert-butyldimethylsilyloxy)-1-methylcyclohexanecarboxylate (Intermediate 66, 1.32 g, 4.39 mmol) was dissolved in THF (25 ml), to which tetrabutylammonium fluoride (TBAF, 1M solution in THF) (7.34 ml, 7.34 mmol) was added. The reaction mixture was stirred at room temperature overnight, then concentrated and the residue was partitioned between EtOAc/water. The aqueous layer was back extracted and combined organics were dried over MgSO4, filtered and concentrated to afford a brown oil. This material was purified via flash column chromatography, eluting with 2-50% EtOAc/Hept. Relevant fractions were pooled and concentrated to afford a clear oil—797 mg (97% yield). was added concentrated the residue was partitioned between EtOAc/water The aqueous layer was back extracted combined organics were dried over MgSO4 filtered concentrated to afford a brown oil This material was purified via flash column chromatography eluting with 2-50% EtOAc/Hept concentrated to afford a clear oil—797 mg (97% yield)