Sodium borohydride → Trans-tert-butyl 2-(hydroxymethyl)-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate

HRID 1034515Notes

Reaction equation

HRID 1034515 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][C@@H:9]1[C:18](OC)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>O1CCCC1.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH2:10][C@@H:9]1[CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 57314304(2R,4S)-1-t-butoxycarbonyl-4-methanesulfonyloxy-2-methoxycarbonylpyrrolidine

Product 1

HCID 50896316Trans-tert-butyl 2-(hydroxymethyl)-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,4S)-1-t-butoxycarbonyl-4-methanesulfonyloxy-2-methoxycarbonylpyrrolidine (3.96 g: 12.2 mmole) in a mixture of tetrahydrofuran (12 ml) and ethanol (18 ml), sodium borohydride (1.85 g: 48.8 mmole) is added in a nitrogen atmosphere under ice cooling. The mixture is stirred for 45 minutes at room temperature to give (2R,4S)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (2.97 g). Yield: 83%. Colorless crystals. mp. 95° to 96° C. NMR δ(CDCl3) ppm: 1.49(s, 9H), 1.7 to 2.1(m, 1H), 2.3 to 2.5(m, 1H), 3.06(s, 3H), 3.4 to 3.7(m, 2H), 3.7 to 4.0(m, 2H), 4.0 to 4.3(m, 1H), 5.2(m, 1H). IR ν (KBr) cm-1 : 3400, 3420, 1648.

Workup

  1. additionis added in a nitrogen atmosphere under ice cooling

Sources & evidence

ORD record
ord-32429bb707e74ec9b691ad9827e945a9
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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