Dimethyl Sulfoxide → tert-butyl N-(4-oxocyclohexyl)carbamate

HRID 22945Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([NH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21][CH2:20]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.C(Cl)Cl>[C:11]([O:15][C:16]([NH:18][CH:19]1[CH2:20][CH2:21][C:22](=[O:25])[CH2:23][CH2:24]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

0.494 ml of DMSO was slowly added dropwise to 10 ml of a methylene chloride solution containing 0.526 ml of oxalyl chloride under argon gas atmosphere at −78° C. After 15 minutes from the completion of the addition, 30 ml of a methylene chloride suspension containing trans-4-tert-butoxycarbonylaminocyclohexanol in was added dropwise, and further 30 minutes later, 2.52 ml of triethylamine was added thereto and the mixture was stirred at −78° C. for 30 minutes and at 0° C. for 15 minutes. An aqueous sodium bicarbonate solution was added to the reaction mixture and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and then, the solvent was removed under reduced pressure. The resulting residue was suspended in a hexane-isopropyl ether mixed solvent and collected by filtration to obtain 0.903 g of 4-(tert-butoxycarbonylamino)cyclohexanone.

Workup

additionin was added dropwise
extractionthe mixture was extracted with chloroform
dry with materialThe extract was dried over anhydrous sodium sulfate
customthe solvent was removed under reduced pressure
filtrationcollected by filtration

Sources & evidence

ORD record: ord-b74f4d3f880243f28596889b283081d2
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849622B2

Reaction notes

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