Benzyl Alcohol → (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarbonyl azide

Participants

Reaction Steps

A stirred solution of (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid (1.0 g, 5.88 mmol) in acetone (20 ml), Et3N (1.6 ml, 11.76 mmol) and ethyl chloroformate (1.12 ml, 11.76 mmol) were added slowly by portion wise at about 0° C. and stirred for about 3 hours. After completion of the reaction (monitored by TLC), NaN3 (0.84 g, 12.93 mmol) dissolved in minimum amount of water was added to reaction mixture at 0° C. and the reaction mixture was allowed to stir at room temperature for about 1.5 hours. After completion of the reaction (monitored by TLC), the reaction mixture was extracted with DCM and washed with water, brine and dried over Na2SO4 and benzyl alcohol (0.95 ml, 8.82 mmol) then the solvent was evaporated and the crude product was processed for next reaction immediately without characterization (considering as 100% yield proceeded for next reaction). Crude wt: 1.147 g (100% yield).

Provenance & Evidence