Sodium borohydride → (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

HRID 1941602Notes

Reaction equation

HRID 1941602 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 107821621,2-Pyrrolidinedicarboxylic acid, 4-[(methylsulfonyl)oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-

Product 1

HCID 53830029(2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanolYield 83.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxy-2-methoxycarbonylpyrrolidine (11.21 g: 34.4 mmole) in a mixture of tetrahydrofuran (34 ml) and ethanol (51 ml), sodium borohydride (5.21 g: 137.7 mmole) is added in a nitrogen atmosphere under ice cooling. The mixture is stirred for 75 minutes at room temperature to give (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (8.47 g). Yield: 83%. Colorless crystals.

Workup

  1. additionis added in a nitrogen atmosphere under ice cooling

Sources & evidence

ORD record
ord-9d9ed2e5ab12401ca5ba189a69491bac
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

Loading…