4-pyrrolidin-1-ylbutan-2-ol

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

Procedure: 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1.03 g, 4.40 mmol), 4-pyrrolidin-1-yl-butan-2-ol (0.5 g, 3.50 mmol), PPh3 (1.15 g, 4.40 mmol), THF (10 ml) and DIAD (0.86 ml, 4.40 mmol) were reacted together according to general procedure C. The crude product was purified by preparative HPLC, eluting with acetonitrile/water/0.1% TFA as a gradient, to give the title compound as a yellow oil (125 mg, 10%). 1H NMR (400 MHz, CDCl3) δ7.19 (d, 2H), 6.86 (d, 2H), 4.43 (m, 1H), 3.75 (dt, 2H), 3.60-3.51 (m, 2H), 2.67-2.46 (m, 6H), 2.40 (s, 2H), 2.14-2.04 (m, 2H), 1.97 (s, 6H), 1.93-1.73 (m, 8H), 1.31 (d, 3H). The crude product was purified by preparative HPLC eluting with acetonitrile/water/0.1% TFA as a gradient

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

Procedure: 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1.03 g, 4.40 mmol), 4-pyrrolidin-1-yl-butan-2-ol (0.5 g, 3.50 mmol), PPh3 (1.15 g, 4.40 mmol), THF (10 ml) and DIAD (0.86 ml, 4.40 mmol) were reacted together according to general procedure C. The crude product was purified by preparative HPLC, eluting with acetonitrile/water/0.1% TFA as a gradient, to give the title compound as a yellow oil (125 mg, 10%). 1H NMR (400 MHz, CDCl3) δ7.19 (d, 2H), 6.86 (d, 2H), 4.43 (m, 1H), 3.75 (dt, 2H), 3.60-3.51 (m, 2H), 2.67-2.46 (m, 6H), 2.40 (s, 2H), 2.14-2.04 (m, 2H), 1.97 (s, 6H), 1.93-1.73 (m, 8H), 1.31 (d, 3H). The crude product was purified by preparative HPLC eluting with acetonitrile/water/0.1% TFA as a gradient

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

Procedure: Pyrrolidine (2 ml, 24 mmol), THF (20 ml) and methyl vinylketone (2.5 ml, 31 mmol) were mixed together and stirred overnight. NaBH4 (1.17 g, 31 mmol) was added to the reaction mixture and stirred for 3 hours. The reaction was quenched with water (20 ml) and extracted with TBME (2×20 ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo. The crude product was purified by column chromatography, eluting with DCM:MeOH:NH3 (94:5:1), to give the title compound as a pale yellow oil (1.3 g, 38%). stirred for 3 hours The reaction was quenched with water (20 ml) extracted with TBME (2×20 ml) The combined organic extracts were dried over MgSO4 filtered washed with TBME concentrated in vacuo The crude product was purified by column chromatography eluting with DCM:MeOH:NH3 (94:5:1)

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

Procedure: Pyrrolidine (2 ml, 24 mmol), THF (20 ml) and methyl vinylketone (2.5 ml, 31 mmol) were mixed together and stirred overnight. NaBH4 (1.17 g, 31 mmol) was added to the reaction mixture and stirred for 3 hours. The reaction was quenched with water (20 ml) and extracted with TBME (2×20 ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo. The crude product was purified by column chromatography, eluting with DCM:MeOH:NH3 (94:5:1), to give the title compound as a pale yellow oil (1.3 g, 38%). stirred for 3 hours The reaction was quenched with water (20 ml) extracted with TBME (2×20 ml) The combined organic extracts were dried over MgSO4 filtered washed with TBME concentrated in vacuo The crude product was purified by column chromatography eluting with DCM:MeOH:NH3 (94:5:1)

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

Procedure: 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1.03 g, 4.40 mmol), 4-pyrrolidin-1-yl-butan-2-ol (0.5 g, 3.50 mmol), PPh3 (1.15 g, 4.40 mmol), THF (10 ml) and DIAD (0.86 ml, 4.40 mmol) were reacted together according to general procedure C. The crude product was purified by preparative HPLC, eluting with acetonitrile/water/0.1% TFA as a gradient, to give the title compound as a yellow oil (125 mg, 10%). 1H NMR (400 MHz, CDCl3) δ7.19 (d, 2H), 6.86 (d, 2H), 4.43 (m, 1H), 3.75 (dt, 2H), 3.60-3.51 (m, 2H), 2.67-2.46 (m, 6H), 2.40 (s, 2H), 2.14-2.04 (m, 2H), 1.97 (s, 6H), 1.93-1.73 (m, 8H), 1.31 (d, 3H). The crude product was purified by preparative HPLC eluting with acetonitrile/water/0.1% TFA as a gradient

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

Procedure: Pyrrolidine (2 ml, 24 mmol), THF (20 ml) and methyl vinylketone (2.5 ml, 31 mmol) were mixed together and stirred overnight. NaBH4 (1.17 g, 31 mmol) was added to the reaction mixture and stirred for 3 hours. The reaction was quenched with water (20 ml) and extracted with TBME (2×20 ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo. The crude product was purified by column chromatography, eluting with DCM:MeOH:NH3 (94:5:1), to give the title compound as a pale yellow oil (1.3 g, 38%). stirred for 3 hours The reaction was quenched with water (20 ml) extracted with TBME (2×20 ml) The combined organic extracts were dried over MgSO4 filtered washed with TBME concentrated in vacuo The crude product was purified by column chromatography eluting with DCM:MeOH:NH3 (94:5:1)

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

Procedure: Pyrrolidine (2 ml, 24 mmol), THF (20 ml) and methyl vinylketone (2.5 ml, 31 mmol) were mixed together and stirred overnight. NaBH4 (1.17 g, 31 mmol) was added to the reaction mixture and stirred for 3 hours. The reaction was quenched with water (20 ml) and extracted with TBME (2×20 ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo. The crude product was purified by column chromatography, eluting with DCM:MeOH:NH3 (94:5:1), to give the title compound as a pale yellow oil (1.3 g, 38%). stirred for 3 hours The reaction was quenched with water (20 ml) extracted with TBME (2×20 ml) The combined organic extracts were dried over MgSO4 filtered washed with TBME concentrated in vacuo The crude product was purified by column chromatography eluting with DCM:MeOH:NH3 (94:5:1)

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

Procedure: 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1.03 g, 4.40 mmol), 4-pyrrolidin-1-yl-butan-2-ol (0.5 g, 3.50 mmol), PPh3 (1.15 g, 4.40 mmol), THF (10 ml) and DIAD (0.86 ml, 4.40 mmol) were reacted together according to general procedure C. The crude product was purified by preparative HPLC, eluting with acetonitrile/water/0.1% TFA as a gradient, to give the title compound as a yellow oil (125 mg, 10%). 1H NMR (400 MHz, CDCl3) δ7.19 (d, 2H), 6.86 (d, 2H), 4.43 (m, 1H), 3.75 (dt, 2H), 3.60-3.51 (m, 2H), 2.67-2.46 (m, 6H), 2.40 (s, 2H), 2.14-2.04 (m, 2H), 1.97 (s, 6H), 1.93-1.73 (m, 8H), 1.31 (d, 3H). The crude product was purified by preparative HPLC eluting with acetonitrile/water/0.1% TFA as a gradient

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

Procedure: Pyrrolidine (2 ml, 24 mmol), THF (20 ml) and methyl vinylketone (2.5 ml, 31 mmol) were mixed together and stirred overnight. NaBH4 (1.17 g, 31 mmol) was added to the reaction mixture and stirred for 3 hours. The reaction was quenched with water (20 ml) and extracted with TBME (2×20 ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo. The crude product was purified by column chromatography, eluting with DCM:MeOH:NH3 (94:5:1), to give the title compound as a pale yellow oil (1.3 g, 38%). stirred for 3 hours The reaction was quenched with water (20 ml) extracted with TBME (2×20 ml) The combined organic extracts were dried over MgSO4 filtered washed with TBME concentrated in vacuo The crude product was purified by column chromatography eluting with DCM:MeOH:NH3 (94:5:1)