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

HRID 515315Notes

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 (23.99 mmol, 4.653 g) and sodium hydride (32.9 mmol, 1.314 g) were combined in tetrahydrofuran and stirred at 0° C. for 30 minutes. tert-Butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (36.0 mmol, 10.05 g) was added and the reaction mixture stirred and heated overnight at 60° C. The reaction mixture was concentrated under vacuum and the residue partitioned between dichloromethane and water, the organic layer was separated, dried, and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with a 0-10% methanol/dichloromethane gradient) to afford the title compound (2.90 g).

Workup

stirringthe reaction mixture stirred
temperatureheated overnight at 60° C
concentrationThe reaction mixture was concentrated under vacuum
customthe residue partitioned between dichloromethane and water
customthe organic layer was separated
customdried
concentrationconcentrated under vacuum
customThe residue was purified by silica column chromatography (
washeluting with a 0-10% methanol/dichloromethane gradient)

Sources & evidence

ORD record: ord-6a5b0a2408e1415a9cc5507056c14e2d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108939B2

Reaction notes

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