Triethylamine → HCID 10746404, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine-2-methanol (22.33 g: 41.37 mmole) is diluted with dichloromethane (300 ml) and the mixture is cooled to -30° C. To this mixture, triethylamine (6.92 ml: 1.2 eq.) and methanesulfonyl chloride (3.52 ml: 1.1 eq.) are added, and the mixture is stirred for 20 minutes. The reaction mixture is successively washed with dilute hydrochloric acid and water, dried over magnesium sulfate, and filtered. The filtrate is concentrated in vacuo to give crude (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine-2-methanol methanesulfonate (27.81 g: 45.02 mmole). Yield: 100%. NMR δ(CDCl3) ppm: 2.89(s, 3H), 3.81, 3.83(2×s, 3H), 4.85 to 5.07(m, 2H). IR ν (CHCl3) cm-1 : 1725, 1690, 1610.

Provenance & Evidence