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

HRID 1365312Notes

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-73e83dd94e2543c7b9d9cf8ba91acb18
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888352B2

Reaction notes

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