Methanol → 4-Phenyl-3-pyrrolidinol

HRID 557918Notes

Reaction equation

HRID 557918 reaction equation
[OH:1][CH:2]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][N:4](C(OCC2C=CC=CC=2)=O)[CH2:3]1.CO>[Pd]>[C:7]1([CH:6]2[CH2:5][NH:4][CH2:3][CH:2]2[OH:1])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 66661829HCID 66661829, compound

Product 1

HCID 533947794-Phenyl-3-pyrrolidinolYield 90.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of benzyl 3-hydroxy-4-phenylpyrrolidine-1-carboxylate (125 mg, 0.000420 mol), palladium (25 mg, 0.000023 mol) in methanol (10 mL, 0.2 mol) was stirred under a H2 atmosphere (balloon with H2) over 2 hours. LCMS indicated that the starting material was consumed. The reaction mixture was filtered and the filtrate was concentrated to yield the product (62 mg). LCMS: m/z 163.9 (M+H+).

Workup

  1. customwas consumed
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-38bff0262612434dbdf0cfbcaa1d554c
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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