Ammonia → tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylate

HRID 567839Notes

Reaction equation

HRID 567839 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)#[N:2].N>[Ni].C(O)C>[NH3:2].[NH2:2][CH2:1][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 7018344(R)-1-Boc-3-cyanopyrrolidine

Product 2

HCID 222AmmoniaHCID 1515152tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylateYield 195.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl (3R)-3-cyano-1-pyrrolidinecarboxylate (preparation 79) (1.60 g, 8.13 mmol) and Raney® Nickel (1 g) in 0.88 ammonia (20 ml) and ethanol (150 ml), was hydrogentaed at 60 psi and room temperature for 8 hrs. The mixture was filtered through Arbocel®, and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (100:0:0 to 90:10:1) to yield the desired product as an oil, (1.59 g, 98%).

Workup

  1. filtrationThe mixture was filtered through Arbocel®
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-1c7a07d975f346d390c3f0a0a6b4b0eb
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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