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

HRID 2170107Notes

Reaction equation

HRID 2170107 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-6aea096867804343ab824bfee7a9e289
Source dataset
uspto-grants-2015_06
Patent number
US09050339B2

Reaction notes

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