Diethyl Ether → HCID 57238975, compound

Participants

Reaction Conditions

Reaction Steps

N-methylmorpholine (1.7 mL, 2.2 equiv) was added to a solution of (2S, 3S)-N-Boc-O-t-butylthreonine (2.0 g, 7.0 mmol, 1.0 equiv) in anhydrous CH2Cl2 (40 mL). The resulting solution was cooled to −15° C. under an argon atmosphere. Iso-butylchloroformate (0.94 mL, 1.03 equiv) was added and the mixture was stirred for 20 min. A solution of diazomethane in Et2O (75 mL, about 67 mmol) was added over 5 min, the cold bath was removed and the reaction was allowed to warm over a 1 h period. Acetic acid was added dropwise until the bubbling stopped. The reaction solution was diluted with CH2Cl2 (150 mL) and washed sequentially with saturated sodium bicarbonate (2×100 mL), water (1×100 mL) and saturated brine (1×100 mL). The organic layer was dried over Na2SO4, decanted and concentrated in vacuo to yield (2S, 3S)-N-Boc-O-t-butyl-threonyldiazomethane as a yellow oil that was used without further purification.

Provenance & Evidence