2-Cyano-2-propyl-pentanoic acid tert-butyl ester → Tert-butyl 2-(aminomethyl)-2-propylpentanoate

HRID 1480953Notes

Reaction equation

HRID 1480953 reaction equation
[C:1]([O:5][C:6](=[O:16])[C:7]([C:14]#[N:15])([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([O:5][C:6](=[O:16])[C:7]([CH2:14][NH2:15])([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 898131562-Cyano-2-propyl-pentanoic acid tert-butyl ester

Product 1

HCID 89812951Tert-butyl 2-(aminomethyl)-2-propylpentanoateYield 70.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-cyano-2-propyl-pentanoic acid tert-butyl ester (6.87 g) and Raney Ni (4 mL in water) in MeOH (200 mL) was stirred at rt under H2 atmosphere (balloon) overnight. Then the reaction mixture was filtered over Celite pad, filtrate was concentrated to give the desired product (4.92 g). 1H NMR in CDCl3, δ in ppm: 2.76 (s, 2H), 1.44 (s, 9H), 1.5-1.1 (m, 8H), 0.91 (t, 6H, J=7.0 Hz).

Workup

  1. filtrationThen the reaction mixture was filtered over Celite pad, filtrate
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-0a74bd710ddb4bb3bf2f74cf65a0ae4a
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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