2,2-二甲基-3-吡咯烷-1-基丙-1-醇

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: 4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (1.29 g, 6.4 mmol), 2,2-dimethyl-3-pyrrolidin-1-yl-propan-1-ol (0.8 g, 5.1 mmol), PPh3 (1.67 g, 6.4 mmol), THF (16 ml) and DIAD (1.25 ml, 6.4 mmol) were reacted together according to general procedure H. The crude material was subjected to chromatography on silica eluting with DCM:MeOH (98:2). The resulting solid was slurried in TBME:heptanes (1:2, 1 ml) to provide the title compound (120 mg, 5%) as a white solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.94 (d, 2H), 4.12-4.03 (m, 2H), 3.89 (td, 2H), 3.71 (s, 2H), 2.57 (br s, 4H), 2.47 (s, 2H), 2.15-1.99 (m, 4H), 1.70 (brs, 4H), 1.00 (s, 6H).

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

实验步骤: 4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (1.29 g, 6.4 mmol), 2,2-dimethyl-3-pyrrolidin-1-yl-propan-1-ol (0.8 g, 5.1 mmol), PPh3 (1.67 g, 6.4 mmol), THF (16 ml) and DIAD (1.25 ml, 6.4 mmol) were reacted together according to general procedure H. The crude material was subjected to chromatography on silica eluting with DCM:MeOH (98:2). The resulting solid was slurried in TBME:heptanes (1:2, 1 ml) to provide the title compound (120 mg, 5%) as a white solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.94 (d, 2H), 4.12-4.03 (m, 2H), 3.89 (td, 2H), 3.71 (s, 2H), 2.57 (br s, 4H), 2.47 (s, 2H), 2.15-1.99 (m, 4H), 1.70 (brs, 4H), 1.00 (s, 6H).

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

实验步骤: Pyrrolidine (1.82 g, 25 mmol), K2CO3 (3.0 g, 1.04 eq.), 3-bromo-2,2-dimethyl-propan-1-ol (8.45 g, 50 mmol, 2 eq.) were heated together at 90° C. overnight. The reaction was allowed to cool to room temperature and quenched with 2M HCl solution (50 ml) and extracted with TBME (3×50 ml). The aqueous phase was basified to pH 14 with 2M NaOH solution and extracted with DCM (3×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give the title compound (1.03 g, 26%) as a pale yellow oil. quenched with 2M HCl solution (50 ml) extracted with TBME (3×50 ml) extracted with DCM (3×50 ml) The combined organic extracts were dried over MgSO4 filtered washed with DCM concentrated in vacuo

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

实验步骤: Pyrrolidine (1.82 g, 25 mmol), K2CO3 (3.0 g, 1.04 eq.), 3-bromo-2,2-dimethyl-propan-1-ol (8.45 g, 50 mmol, 2 eq.) were heated together at 90° C. overnight. The reaction was allowed to cool to room temperature and quenched with 2M HCl solution (50 ml) and extracted with TBME (3×50 ml). The aqueous phase was basified to pH 14 with 2M NaOH solution and extracted with DCM (3×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give the title compound (1.03 g, 26%) as a pale yellow oil. quenched with 2M HCl solution (50 ml) extracted with TBME (3×50 ml) extracted with DCM (3×50 ml) The combined organic extracts were dried over MgSO4 filtered washed with DCM concentrated in vacuo

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

实验步骤: 4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (1.29 g, 6.4 mmol), 2,2-dimethyl-3-pyrrolidin-1-yl-propan-1-ol (0.8 g, 5.1 mmol), PPh3 (1.67 g, 6.4 mmol), THF (16 ml) and DIAD (1.25 ml, 6.4 mmol) were reacted together according to general procedure H. The crude material was subjected to chromatography on silica eluting with DCM:MeOH (98:2). The resulting solid was slurried in TBME:heptanes (1:2, 1 ml) to provide the title compound (120 mg, 5%) as a white solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.94 (d, 2H), 4.12-4.03 (m, 2H), 3.89 (td, 2H), 3.71 (s, 2H), 2.57 (br s, 4H), 2.47 (s, 2H), 2.15-1.99 (m, 4H), 1.70 (brs, 4H), 1.00 (s, 6H).

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

实验步骤: 4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (1.29 g, 6.4 mmol), 2,2-dimethyl-3-pyrrolidin-1-yl-propan-1-ol (0.8 g, 5.1 mmol), PPh3 (1.67 g, 6.4 mmol), THF (16 ml) and DIAD (1.25 ml, 6.4 mmol) were reacted together according to general procedure H. The crude material was subjected to chromatography on silica eluting with DCM:MeOH (98:2). The resulting solid was slurried in TBME:heptanes (1:2, 1 ml) to provide the title compound (120 mg, 5%) as a white solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.94 (d, 2H), 4.12-4.03 (m, 2H), 3.89 (td, 2H), 3.71 (s, 2H), 2.57 (br s, 4H), 2.47 (s, 2H), 2.15-1.99 (m, 4H), 1.70 (brs, 4H), 1.00 (s, 6H).

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

实验步骤: Pyrrolidine (1.82 g, 25 mmol), K2CO3 (3.0 g, 1.04 eq.), 3-bromo-2,2-dimethyl-propan-1-ol (8.45 g, 50 mmol, 2 eq.) were heated together at 90° C. overnight. The reaction was allowed to cool to room temperature and quenched with 2M HCl solution (50 ml) and extracted with TBME (3×50 ml). The aqueous phase was basified to pH 14 with 2M NaOH solution and extracted with DCM (3×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give the title compound (1.03 g, 26%) as a pale yellow oil. quenched with 2M HCl solution (50 ml) extracted with TBME (3×50 ml) extracted with DCM (3×50 ml) The combined organic extracts were dried over MgSO4 filtered washed with DCM concentrated in vacuo

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: 4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (1.29 g, 6.4 mmol), 2,2-dimethyl-3-pyrrolidin-1-yl-propan-1-ol (0.8 g, 5.1 mmol), PPh3 (1.67 g, 6.4 mmol), THF (16 ml) and DIAD (1.25 ml, 6.4 mmol) were reacted together according to general procedure H. The crude material was subjected to chromatography on silica eluting with DCM:MeOH (98:2). The resulting solid was slurried in TBME:heptanes (1:2, 1 ml) to provide the title compound (120 mg, 5%) as a white solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.94 (d, 2H), 4.12-4.03 (m, 2H), 3.89 (td, 2H), 3.71 (s, 2H), 2.57 (br s, 4H), 2.47 (s, 2H), 2.15-1.99 (m, 4H), 1.70 (brs, 4H), 1.00 (s, 6H).

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

实验步骤: Pyrrolidine (1.82 g, 25 mmol), K2CO3 (3.0 g, 1.04 eq.), 3-bromo-2,2-dimethyl-propan-1-ol (8.45 g, 50 mmol, 2 eq.) were heated together at 90° C. overnight. The reaction was allowed to cool to room temperature and quenched with 2M HCl solution (50 ml) and extracted with TBME (3×50 ml). The aqueous phase was basified to pH 14 with 2M NaOH solution and extracted with DCM (3×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give the title compound (1.03 g, 26%) as a pale yellow oil. quenched with 2M HCl solution (50 ml) extracted with TBME (3×50 ml) extracted with DCM (3×50 ml) The combined organic extracts were dried over MgSO4 filtered washed with DCM concentrated in vacuo