Tert-butyl 4-(methylsulfonyl)piperidine-1-carboxylate → tert-Butyl 4-(acetylthio)piperidine-1-carboxylate

HRID 881413Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](S(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([O-:21])(=[S:20])[CH3:19].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:20][C:18](=[O:21])[CH3:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-methanesulfonyl-piperidine-carboxylic acid tert-butyl ester (2.82 g), sodium thioacetate (2.31 g) and DMF (40 ml) was stirred at 60° C. After 4 hours the reaction mixture was cooled and partitioned between ethyl acetate and brine. The combined organics were dried (MgSO4) and the solvents removed in vacuo. The resulting crude mixture was purified by flash chromatography to yield 4-acetylsulfanyl-piperidine-1-carboxylic acid tert-butyl ester (1.8 g).

Workup

temperatureAfter 4 hours the reaction mixture was cooled
custompartitioned between ethyl acetate and brine
dry with materialThe combined organics were dried (MgSO4)
customthe solvents removed in vacuo
customThe resulting crude mixture was purified by flash chromatography

Sources & evidence

ORD record: ord-8d9f99504b8b4a41aa335c86119931aa
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993563B2

Reaction notes

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