Triethylamine → HCID 178457364, compound

Participants

Reaction Steps

90 ml mesyl chloride was added with stirring to a previously chilled (-10°) solution of (2S)-3-isopropylamino-1,2-propanediol acetonide (188 g; 1.087 mol) and triethylamine (228 ml; 1.63 mol) in dry tetrahydrofuran at such a rate that the reaction temperature did not exceed 5°. Reaction was then stirred at 10°-15° for 30 minutes whereupon it was diluted with 1.5 L brine. The layers were separated and the aqueous layers were extracted with ether (3×500 ml). The organic layers were washed in turn with brine (2×500 ml) and then were combined, dried over sodium sulfate, and evaporated to give 264 g of (2S)-3-[N-mesyl-(1-methylethyl)amino]-1,2-propanediol acetonide as an oil.

Provenance & Evidence