Nitromethane → tert-Butyl 3-hydroxy-3-(nitromethyl)azetidine-1-carboxylate

HRID 1803054Notes

Reaction equation

HRID 1803054 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:13]([CH3:16])([O-:15])=[O:14].C(N(CC)CC)C>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([OH:12])([CH2:16][N+:13]([O-:15])=[O:14])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8471TriethylamineHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 57415904tert-Butyl 3-hydroxy-3-(nitromethyl)azetidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Oxoazetidine-1-carboxylic acid tert-butyl ester (500 mg, 2.9 mmol) was dissolved in ethanol (1.5 mL) and to this was added nitromethane (0.6 mL) and triethylamine (cat.). The reaction was stirred for eighteen hours and the solvent was then removed under reduced pressure to yield the title compound as a white solid (650 mg, 97%). δH (d6-DMSO) 6.42 (1H, s), 4.86 (2H, s), 4.04 (2H, d, J 9.2 Hz), 3.75 (2H, d, J 9.2 Hz), 1.39 (9H, s). LCMS (ES+) RT (pH 10) 1.73 min (M−H)− 231.

Workup

  1. customthe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-2c39a6569bf747fd88d1edcfb9a6584b
Source dataset
uspto-grants-2013_01
Patent number
US08350037B2

Reaction notes

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