Dimethyl Sulfoxide → 2(S)-Tert-butoxycarbonylamino-6-triisopropylsilyloxy-4,4-dimethyl-hexanal

Participants

Reaction Conditions

Reaction Steps

14.7 ml of dimethylsulfoxide in 200 ml of methylene chloride are added dropwise to a solution of 13.4 ml of oxalyl chloride in 200 ml of methylene chloride at -60° C. After 15 min, a solution of 43.2 g of 2(S)-tert-butoxycarbonylamino-6-triisopropylsilyloxy-4,4-dimethyl-hexan-1-ol in 320 ml of methylene chloride is added dropwise at -60° C. in the course of 40 min, while stirring vigorously. 58 ml of triethylamine are then added and the reaction mixture is stirred at -60° C. for 90 min. It is allowed to warm to -10° C., 200 ml of a 20% potassium hydrogen sulfate solution are added, the mixture is subsequently stirred briefly and the product is extracted with methylene chloride. This gives 43 g of the title compound, which is reacted further without additional purification: Rf (A)=0.62, Rf (D)=0.3; Rt (II)=34.8 min.

Provenance & Evidence