4-Nitrobenzenethiol → Tert-butyl 4-[(4-nitrophenyl)sulfanyl]piperidine-1-carboxylate

HRID 515321Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].CS(O[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)(=O)=O>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Nitrobenzenethiol (5.93 mmol, 1.15 g), and sodium hydride (8.12 mmol, 0.325 g) were combined in tetrahydrofuran and stirred at 0° C. for 30 minutes. tert-Butyl 4-(methyl-sulfonyloxy)piperidine-1-carboxylate (8.89 mmol, 2.484 g) was added and the reaction mixture heated at 60° C. overnight. The reaction mixture was concentrated under vacuum and residue dissolved in dichloromethane and washed with water. The organic layer was separated, dried and concentrated under vacuum. The residue was purified by silica column chromatography (eluent: dichloromethane) to afford the title compound (1.45 g). MS (ESI) m/z 339.5 [M+H]+

Workup

temperaturethe reaction mixture heated at 60° C. overnight
concentrationThe reaction mixture was concentrated under vacuum and residue
dissolutiondissolved in dichloromethane
washwashed with water
customThe organic layer was separated
customdried
concentrationconcentrated under vacuum
customThe residue was purified by silica column chromatography (eluent: dichloromethane)

Sources & evidence

ORD record: ord-b8c4e3c523cf408fb4db7e8423dd5619
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108939B2

Reaction notes

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