Carbon Dioxide → tert-butyl N-methyl-N-[trans-4-formylcyclohexyl]carbamate

HRID 25589Notes

Reaction equation

HRID 25589 reaction equation
C(=O)=O.CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:14]([O:18][C:19](=[O:30])[N:20]([C@H:22]1[CH2:27][CH2:26][C@H:25]([CH2:28][OH:29])[CH2:24][CH2:23]1)[CH3:21])([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC>C(Cl)Cl>[C:14]([O:18][C:19](=[O:30])[N:20]([CH:22]1[CH2:23][CH2:24][CH:25]([CH:28]=[O:29])[CH2:26][CH2:27]1)[CH3:21])([CH3:15])([CH3:17])[CH3:16]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178486045HCID 178486045, compound

Product 1

HCID 86584984tert-butyl N-methyl-N-[trans-4-formylcyclohexyl]carbamateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dry-ice cooled solution of 8.94 ml (125.9 mmol) DMSO in 150 ml CH2Cl2 was added 5.95 ml (69.24 mmol) oxalylchloride. After 5 min at −78° C., a solution of 16.2 g (66.5 mmol) trans-(4-Hydroxymethyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester in 50 ml of CH2Cl2, was added slowly. 10 min later, 43.8 ml (314.75 mmol) of Et3N was added, and the mixture was allowed to attain RT. The mixture was partitioned between Et2O/1N HCl and water. The solvent was evaporated under reduced pressure yielding 16.12 g of clean (4-Formyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester, MS: 241 (m).

Workup

  1. customto attain RT
  2. customThe mixture was partitioned between Et2O/1N HCl and water
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-09d10b739a05479196e4a9098b444134
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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