1-tert-Butyl 2-methyl (2S,4R)-4-cyanopyrrolidine-1,2-dicarboxylate → 1-(tert-Butyl) 2-methyl (2S,4S)-4-(aminomethyl)pyrrolidine-1,2-dicarboxylate

HRID 2185425Notes

Reaction equation

HRID 2185425 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@@H:4]1[CH2:8][C@@H:7]([C:9]#[N:10])[CH2:6][N:5]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(O)C.[Ni]>[CH3:1][O:2][C:3](=[O:18])[C@@H:4]1[CH2:8][C@@H:7]([CH2:9][NH2:10])[CH2:6][N:5]1[C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12]

Participants

4

Reactant 1

HCID 179989661-tert-Butyl 2-methyl (2S,4R)-4-cyanopyrrolidine-1,2-dicarboxylate

Product 1

HCID 541001131-(tert-Butyl) 2-methyl (2S,4S)-4-(aminomethyl)pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-tert-butoxycarbonyl-trans-4-cyano-L-proline methyl ester (A, 197 mg) and Raney-Ni (100 mg) in ethanol (6 mL) was stirred at room temperature for 21 hr under hydrogen. The catalysts were removed by filtration and washed with ethanol. The filtrate was evaporated in vacuo to give the title compound (204 mg).

Workup

  1. customThe catalysts were removed by filtration
  2. washwashed with ethanol
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-db421577c41f4ae389dc81986eb8b9d0
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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