tert-butyl N-(4-oxocyclohexyl)carbamate → Tert-butyl 4-(tert-butylsulfinylimino)cyclohexylcarbamate

HRID 246650Notes

Reaction equation

O=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[CH3:16][C:17]([S:20]([NH2:22])=[O:21])([CH3:19])[CH3:18]>C1COCC1>[C:17]([S:20]([N:22]=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1)=[O:21])([CH3:19])([CH3:18])[CH3:16]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of tert-butyl 4-oxocyclohexylcarbamate (1.0 g, 4.7 mmol), 2-methylpropane-2-sulfinamide (0.63 g, 5.17 mmol) and Ti(OEt)4 (2.1 g, 9.2 mmol) in 10 mL of THF was stirred at 50-60° C. overnight. The mixture was cooled to room temperature and the residue purified by column chromatography (silica gel, 200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (4:1, v/v) to give tert-butyl 4-(tert-butylsulfinylimino)cyclohexylcarbamate (1.0 g, 67%) as an clear oil. MS: (M+H)+=317.3; 1H NMR (300 MHz, CDCl3): δ 4.88-4.86 (m, 1H), 3.83 (brs, 1H), 3.39-3.38 (m, 1H), 2.62-2.15 (m, 5H), 1.68-1.53 (m, 2H), 1.43 (s, 9H), 1.24 (s, 9H).

Workup

temperatureThe mixture was cooled to room temperature
customthe residue purified by column chromatography (silica gel, 200-300 mesh
washeluting with a mixture of petroleum ether and ethyl acetate (4:1

Sources & evidence

ORD record: ord-adb60c4cd1774ff3ad8097427af5df33
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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