Ammonia → HCID 59558354, compound

HRID 1175134Notes

Reaction equation

HRID 1175134 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=[CH:12][C:13]([O:15][CH3:16])=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:17]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([NH2:17])([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 56923823tert-Butyl 3-(2-methoxy-2-oxoethylidene)azetidine-1-carboxylate

Product 1

HCID 59558354HCID 59558354, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methoxycarbonylmethylene-azetidine-1-carboxylic acid tert-butyl ester (1.97 g; 8.7 mmol) in EtOH (20 ml) and liquid NH3 (11 g) are heated in a steel cylinder at 800 C for 6 hours. Evaporation of the solvent delivers the title compound as yellow resin. 1H-NMR (400 MHz; DMSO-d6): 3.81 (d, 2H); 3.65 (s, 2H); 3.60 (d, 2H); 2.86 (s, 3H); 2.07 (bs, 2H); 1.43 (s, 9H). MS (m/z) ES+: 245 (100, MH+); 189 (90).

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-207938e7e99042c6b3781dd2981d076f
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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