1-tert-Butyl 3-ethyl 3-cyanoazetidine-1,3-dicarboxylate → 1-(1,1-Dimethylethyl) 3-methyl 3-(aminomethyl)-1,3-azetidinedicarboxylate

HRID 1175153Notes

Reaction equation

HRID 1175153 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:17]#[N:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5])C.[H][H]>CO.[Ni]>[CH3:1][O:3][C:4]([C:6]1([CH2:17][NH2:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:7]1)=[O:5]

Participants

5

Reactant 2

HCID 595585001-tert-Butyl 3-ethyl 3-cyanoazetidine-1,3-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 595583501-(1,1-Dimethylethyl) 3-methyl 3-(aminomethyl)-1,3-azetidinedicarboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

3-Cyano-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (7.75 g; 30.5 mmol) in methanol (1000 ml) is combined with wet RaNi (˜28 g) and hydrogenated at room temperature under 1 atm of hydrogen for 2 hours. The reaction mixture is filtered and evaporated to dryness to yield the title compound as light brown resin, which crystallizes slowly (6.8 g; 91%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-378a6e0e38bf434db0c6f29381c8ff71
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

Loading…