Acetone Cyanohydrin → HCID 86596973, compound

Participants

Reaction Conditions

Reaction Steps

Examples 11p and 11q, Step 4: To a solution of triphenylphosphine (4.47 g, 17.04 mmoles) in 50 ml of anhydrous THF at −20° C. was added 7.41 ml of 40% solution of diethyl azodicarboxylate in THF (17.04 mmoles) dropwise, and the mixture was stirred for 20 minutes at −20° C. Then to the mixture was added a solution of tert-butyl (1R,3R,4S)-4-(dibenzylamino)-3-(hydroxymethyl)cyclohexylcarbamate (1.81 g, 4.26 mmoles) in 20 ml of anhydrous THF, and it was stirred for 20 minutes at −20° C. At the end of the stirring was added 20 ml of anhydrous THF followed by acetone cyanohydrine (1.56 ml, 17.04 mmoles), and it was continued to stir for 1.5 hours while gradually raising the temperature to 8° C. The reaction was quenched by several drops of methanol, and the solvent was evaporated off. The residue was purified by column chromatography (silica gel, 25:75 EtOAc and hexane) to give 1.87 g of tert-butyl (1R,3S,4S)-3-(cyanomethyl)-4-(dibenzylamino)cyclohexylcarbamate.

Provenance & Evidence