Dimethyl Sulfoxide → Benzyl [(1r,2r)-2-formylcyclohexyl]carbamate

HRID 1592336Notes

Reaction equation

HRID 1592336 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19](=[O:29])[NH:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[CH2:27][OH:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C:19](=[O:29])[NH:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[CH:27]=[O:28])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 24720936Benzyl trans-(2-hydroxymethyl)cyclohexylcarbamate

Product 1

HCID 29923903Benzyl [(1r,2r)-2-formylcyclohexyl]carbamateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of oxalyl chloride (2.6 mL, 29.4 mmol) in dichloromethane (80 mL) at −78° C. was treated with a solution of dimethyl sulfoxide (4.3 mL, 60.8 mmol) in dichloromethane (10 mL) over 5 minutes. The mixture was stirred for 40 min, then treated with a solution of benzyl[(1R,2R)-2-(hydroxymethyl)cyclohexyl]carbamate (5.0 g, 19 mmol) in dichloromethane (20 mL) over 5 minutes. The mixture was stirred for 45 minutes, then was treated with triethylamine (8.6 mL, 61.7 mmol) and allowed to warm to room temperature. After 60 minutes, the mixture was washed with water, then with brine, and dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography using 30% ethyl acetate in hexane to provide a white solid (4.8 g, 97%).

Workup

  1. stirringThe mixture was stirred for 45 minutes
  2. waitAfter 60 minutes
  3. washthe mixture was washed with water
  4. dry with materialwith brine, and dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-2ab0c87a156d407985ea7433715f7980
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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