Hydrochloric Acid → HCID 86623926, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round-bottomed flask, a solution of N,O-dimethyl hydroxylamine HCl was suspended in 20 mL of dichloromethane. After cooling to 0° C., trimethyl aluminum (2 M in toluene. 3.83 mL, 7.66 mmol) was added dropwise and the mixture was stirred at 0° C. for 45 min. A solution of the previously described (1R*,5R*,6R*)-2-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid tert-butyl ester (0.3 g, 1 mmol) in 10 mL of dichloromethane was added dropwise to the cooled stirring solution. After stirring at 0° C. for 5 min, the reaction mixture was warmed to room temperature and stirred for 3 hours. After the reaction was completed, the reaction mixture was again cooled in an ice bath and acidified with 10 mL of 1N HCl, extracted with dichloromethane (×3), dried over MgSO4 and concentrated to afford 0.32 g (86%) of the desired product as a clear oil.

Provenance & Evidence