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

HRID 386710Notes

Reaction equation

HRID 386710 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-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of Raney Ni (0.6 g, 13.19 mmol) in MeOH (30 ml) in a hydrogenation steel pressure vessel was treated with 1-cyano-cyclobutanecarboxylic acid tert-butyl ester (2.39 g, 13.19 mmol). The reaction mixture was placed under an atmosphere of hydrogen (3 bar) overnight. The mixture was filtered and concentrated in vacuo. The residue was dissolved in MeOH and passed through a 20 g Isolute® SCX-2 cartridge. The cartridge was washed with MeOH followed by product 7M ammonia in MeOH. The ammonia washings were concentrated in vacuo to afford the title product which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 2.45 (2H, m), 2.01-1.67 (6H, m), 0.49 (9H, s).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH
  4. washThe cartridge was washed with MeOH
  5. concentrationThe ammonia washings were concentrated in vacuo

Sources & evidence

ORD record
ord-03cd5e29c1564aa8be7b08b923a6c2e4
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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