1-Benzyl-4-phenyl-3-pyrrolidinemethanol → (4-Phenylpyrrolidin-3-yl)methanol
Reaction equation
C([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH2:19][OH:20])[CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2]>[OH:20][CH2:19][CH:10]1[CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][NH:8][CH2:9]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 302 mg (1.1 mmol) of 1-benzyl-3-(SR)-hydroxymethyl-4-(SR)-phenylpyrrolidine (from Example 1, Step B) and 154 mg of 20% Pd(OH)2/C was hydrogenated at 40 psi on a Paar apparatus for 1 h. The catalyst was filtered and the filtrate was concentrated in vacuo to afford 196 mg (98%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ2.53-2.57 (m, 2H), 3.06-3.60 (6H), 7.24-7.35 (5H). Mass Spectrum (NH3-CI): m/z 178 (M+1).
Workup
- filtrationThe catalyst was filtered