tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate → (S)-tert-butyl tetrahydro-2H-pyran-3-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

((S)-4-Hydroxy-1-hydroxymethyl-butyl)-carbamic acid tert-butyl ester (100 mg, 0.46 mmol) was dissolved in warm benzene (1.5 ml). Cyanomethylenetributylphosphorane (165 mg, 0.68 mmol) was added and the reaction vessel was sealed and stirred at 100° C. for 24 h. The reaction was cooled, evaporated and purified by silica gel chromatography (ethyl acetate/hexanes) to give 64 mg (69%) of (S)-(tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester. (M+Na)+=224.

Provenance & Evidence