Methanol → HCID 10589967, compound

HRID 1034491Notes

Reaction equation

C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O.[BH4-].[Na+].CO>O1CCCC1>[C:18]([O:17][C:15]([N:6]1[CH2:7][C@H:8]([O:10][S:11]([CH3:14])(=[O:12])=[O:13])[CH2:9][C@H:5]1[CH2:3][OH:2])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

temperatureThe mixture is cooled with ice
filtrationfiltered
concentrationThe filtrate is concentrated
additiondiluted with ethyl acetate
washwashed with water
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue is recrystallized from petroleum ether-ether

Sources & evidence

ORD record: ord-94582561ab1046dea49ff2dbd54fc743
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05317016

Reaction notes

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