Tert-butyl 1-cyanocyclobutane-1-carboxylate → Tert-butyl 1-(aminomethyl)cyclobutane-1-carboxylate

HRID 1480981Notes

Reaction equation

HRID 1480981 reaction equation
[C:1]([O:5][C:6]([C:8]1([C:12]#[N:13])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([O:5][C:6]([C:8]1([CH2:12][NH2:13])[CH2:9][CH2:10][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66797886Tert-butyl 1-cyanocyclobutane-1-carboxylate

Product 1

HCID 66797588Tert-butyl 1-(aminomethyl)cyclobutane-1-carboxylateYield 83.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-cyano-cyclobutanecarboxylic acid tert-butyl ester (6.58 g) and Raney Ni (10 mL in water) in MeOH (250 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 (5.59 g). 1H NMR in CDCl3, δ in ppm: 2.94 (s, 2H), 2.4-2.2 (m, 2H), 2.0-1.8 (m, 4H), 1.46 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-ee08ce27732843fb9c3b2c24802a01fa
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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