3-(1-Azidoethyl)-3-fluoropyrrolidine-1-carboxylic acid benzyl ester → 3-(1-Aminoethyl)-3-fluoropyrrolidine-1-carboxylic acid benzyl ester

HRID 729437Notes

Reaction equation

HRID 729437 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([CH:17]([N:19]=[N+]=[N-])[CH3:18])([F:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Ni]>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([CH:17]([NH2:19])[CH3:18])([F:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 866071343-(1-Azidoethyl)-3-fluoropyrrolidine-1-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 690766503-(1-Aminoethyl)-3-fluoropyrrolidine-1-carboxylic acid benzyl esterYield 90.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(1-azidoethyl)-3-fluoropyrrolidine-1-carboxylic acid benzyl ester (Example A16, 0.16 g, 0.5 mmol) in methanol (10 mL) is treated with Raney nickel (100 mg, wet weight) and shaken in a hydrogen atmosphere at room temperature and at 55 psi for 17 hours. The catalyst is removed by filtration through Celite, and the solvent is removed in vacuo to afford the title compound (0.12 g). 1H NMR (200 MHz, CDCl3): δ 7.30 (s, 5H), 5.12 (s, 2H), 3.84-3.22 (m, 5H), 2.23-1.79 (m, 4H), 1.20 (d, 3H).

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e625f7348ff848af82c02f5164920cd5
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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