Triethylamine → tert-Butyl (3R)-3-[(methanesulfonyl)oxy]piperidine-1-carboxylate

HRID 1435962Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([OH:19])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl.C(=O)([O-])O.[Na+]>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 2 °C

Procedure

Methanesulfonyl chloride (1.73 ml, 22.5 mmol) was added to a cooled (ice bath, 0-4° C.), stirred solution of (R)-3-hydroxy-piperidine-carboxylic acid tert-butyl ester (3.0 g, 15 mmol) and triethylamine (3.12 ml, 22.5 mmol) in dichloromethane (30 ml). Following the addition the reaction was stirred at this temperature for 30 minutes before being allowed to warm to ambient temperature. After stirring at ambient temperature for 2 hours, aqueous sodium hydrogen carbonate (50 ml) was added, followed by vigorous stirring for 30 minutes. The reaction was diluted with dichloromethane (300 ml) and aqueous sodium hydrogen carbonate (300 ml) and after partitioning the organic phase was washed with water (200 ml), dried with magnesium sulphate and evaporated to dryness under reduced pressure to yield (R)-3-methanesulfonyloxypiperidine-1-carboxylic acid tert-butyl ester as a semi-crystalline solid.

Workup

additionthe addition the reaction
temperatureto warm to ambient temperature
stirringAfter stirring at ambient temperature for 2 hours
stirringby vigorous stirring for 30 minutes
customafter partitioning the organic phase
washwas washed with water (200 ml)
dry with materialdried with magnesium sulphate
customevaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-8b23d3a5ba2642638618041e808511a2
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618985B2

Reaction notes

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