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

HRID 1809939Notes

Reaction equation

HRID 1809939 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=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(N(CC)CC)C>C(Cl)Cl.O>[O:25]=[C:22]1[CH2:21][CH2:20][CH:19]([NH:18][C:16](=[O:17])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178418329HCID 178418329, compound

Product 1

HCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateYield 91.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

To a solution of oxalyl chloride (2.33 mL, 26.7 mmol) in methylene chloride (50 mL) cooled at −60° C. was added a solution of DMSO (4 mL, 56 mmol) in methylene chloride (5 mL) followed by a solution of trans-4-tert-butoxycarbonylaminocyclohexanol (5 g, 23 mmol) obtained above in methylene chloride (20 mL). After stirring at −60° C. for 20 minutes, triethylamine (16.1 mL, 116 mmol) was added. The mixture was allowed to warm to room temperature and stirring was continued for 30 minutes. Water was added. The organic phase was separated and the aqueous layer was extracted with methylene chloride twice. The combined organic phase was washed with brine, dried over MgSO4 and concentrated. Flash chromatography eluting with a gradient of 3% to 5% to 10% MeOH/CH2Cl2 provided 4.5 g (90%) of the title compound. MS (M+H)+214. Found 236 (M+Na)+.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. customThe organic phase was separated
  5. extractionthe aqueous layer was extracted with methylene chloride twice
  6. washThe combined organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. washFlash chromatography eluting with a gradient of 3% to 5% to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a719d84c28124ac3aa65be91defaa6fa
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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