1-benzyl-4-(2-hydroxyethyl)piperidin-4-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of compound 25 (1.32 g, 5.30 mmol) in methanol (10 mL) under argon was added palladium hydroxide (20%) on activated charcoal (132 mg, 10% w/w). The solution was purged three times with hydrogen and stirred under hydrogen atmosphere at 60° C. for 4 hrs. The resulting solution was then filtered on celite plug to give desired compound 26 (790 mg, 94%) which was used as such for the next step. The solution was purged three times with hydrogen The resulting solution was then filtered on celite plug

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of compound 24 (1.70 g, 6.07 mmol) in anhydrous THF (40 mL) at 0° C. was slowly added a solution of lithium aluminium hydride (1.0M in THF) (12.1 mL, 12.1 mmol). The solution was then stirred at 0° C. for 1 hr and allowed to return to room temperature to be stirred for an additional 2 hrs. The resulting solution was poured in a cold 10% solution of sodium sulphate (300 mL), extracted with diethyl ether (3×75 mL), washed with brine and finally dried over magnesium sulphate to give the crude compound 25 (1.32 g, 87%) which was used as such in the next step. 1H NMR (400 MHz, MeOD) δ: 1.65 (m, 4H), 1.72 (t, 2H, J=7.06 Hz), 2.45 (m, 2H), 2.62 (m, 2H), 3.56 (s, 2H), 3.76 (t, 2H, J=7.06 Hz), 7.31 (m, 5H). to return to room temperature to be stirred for an additional 2 hrs extracted with diethyl ether (3×75 mL) washed with brine finally dried over magnesium sulphate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of compound 24 (1.70 g, 6.07 mmol) in anhydrous THF (40 mL) at 0° C. was slowly added a solution of lithium aluminium hydride (1.0M in THF) (12.1 mL, 12.1 mmol). The solution was then stirred at 0° C. for 1 hr and allowed to return to room temperature to be stirred for an additional 2 hrs. The resulting solution was poured in a cold 10% solution of sodium sulphate (300 mL), extracted with diethyl ether (3×75 mL), washed with brine and finally dried over magnesium sulphate to give the crude compound 25 (1.32 g, 87%) which was used as such in the next step. 1H NMR (400 MHz, MeOD) δ: 1.65 (m, 4H), 1.72 (t, 2H, J=7.06 Hz), 2.45 (m, 2H), 2.62 (m, 2H), 3.56 (s, 2H), 3.76 (t, 2H, J=7.06 Hz), 7.31 (m, 5H). to return to room temperature to be stirred for an additional 2 hrs extracted with diethyl ether (3×75 mL) washed with brine finally dried over magnesium sulphate

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of compound 25 (1.32 g, 5.30 mmol) in methanol (10 mL) under argon was added palladium hydroxide (20%) on activated charcoal (132 mg, 10% w/w). The solution was purged three times with hydrogen and stirred under hydrogen atmosphere at 60° C. for 4 hrs. The resulting solution was then filtered on celite plug to give desired compound 26 (790 mg, 94%) which was used as such for the next step. The solution was purged three times with hydrogen The resulting solution was then filtered on celite plug

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of compound 24 (1.70 g, 6.07 mmol) in anhydrous THF (40 mL) at 0° C. was slowly added a solution of lithium aluminium hydride (1.0M in THF) (12.1 mL, 12.1 mmol). The solution was then stirred at 0° C. for 1 hr and allowed to return to room temperature to be stirred for an additional 2 hrs. The resulting solution was poured in a cold 10% solution of sodium sulphate (300 mL), extracted with diethyl ether (3×75 mL), washed with brine and finally dried over magnesium sulphate to give the crude compound 25 (1.32 g, 87%) which was used as such in the next step. 1H NMR (400 MHz, MeOD) δ: 1.65 (m, 4H), 1.72 (t, 2H, J=7.06 Hz), 2.45 (m, 2H), 2.62 (m, 2H), 3.56 (s, 2H), 3.76 (t, 2H, J=7.06 Hz), 7.31 (m, 5H). to return to room temperature to be stirred for an additional 2 hrs extracted with diethyl ether (3×75 mL) washed with brine finally dried over magnesium sulphate