Methanol → HCID 10589967, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylic acid methyl ester (8.11 g) in tetrahydrofuran (49 ml) stirring under ice cooling, sodium borohydride (2.36 g) and methanol (20 ml) are added. The mixture is stirred at room temperature for 25 minutes and at 60° C. for 25 minutes. The mixture is cooled with ice and filtered. The filtrate is concentrated, diluted with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated in vacuo. The residue is recrystallized from petroleum ether-ether to give (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (5.96 g). Colorless crystals. Yield: 80%. mp. 95° to 96° C. NMR δ(CDCl3) ppm: 1.48(s, 9H), 1.78 to 2.02(m, 1H), 2.3 to 2.48(m, 1H), 3.05(s, 3H), 3.5 to 3.65(m, 2H), 3.65 to 4.0(m, 2H), 4.03 to 4.25(m, 1H), 5.2(s, 1H). IR ν (CHCl3) cm-1 : 3460, 1680.

Provenance & Evidence