1-Benzyl-4-phenyl-3-pyrrolidinemethanol → (4-Phenylpyrrolidin-3-yl)methanol

HRID 1276486

Reaction equation

HRID 1276486 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]1

Participants

3

Reactant 1

HCID 219127561-Benzyl-4-phenyl-3-pyrrolidinemethanol

Product 1

HCID 13316928(4-Phenylpyrrolidin-3-yl)methanolYield 100.5%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

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

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9bf2a641b70a47dc8deafdc03379aca3
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Linked notes

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