3-Pyrrolidinecarboxylic acid, 4-cyclopropyl-1-(phenylmethyl)-, methyl ester → HCID 68646753, compound

HRID 1162724Notes

Reaction equation

HRID 1162724 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:9]([CH:10]2[CH2:12][CH2:11]2)[CH2:8][N:7](CC2C=CC=CC=2)[CH2:6]1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH:9]([CH:10]2[CH2:12][CH2:11]2)[CH2:8][NH:7][CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 686476703-Pyrrolidinecarboxylic acid, 4-cyclopropyl-1-(phenylmethyl)-, methyl ester

Product 1

HCID 68646753HCID 68646753, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

101.2 To a stirred solution of 1.13 g (3RS,4RS)-1-benzyl-4-cyclopropyl-pyrrolidine-3-carboxylic acid methyl ester at r.t. in 10 ml methanol under an argon atmosphere was added 113 mg 10% Pd/C. The mixture was then stirred at r.t. under a hydrogen atmosphere overnight. The catalyst was filtered off and rinsed with methanol. The filtrate was concentrated to leave 630 mg (3RS,4RS)-4-cyclopropyl-pyrrolidine-3-carboxylic acid methyl ester as a light yellow oil. MS170.3 ([M+H]+)

Workup

  1. filtrationThe catalyst was filtered off
  2. washrinsed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-326128ba9de0496c9db24ebe38b2f4e5
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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