Methanol → tert-butyl N-methyl-N-(2-oxoethyl)carbamate

HRID 2113551Notes

Reaction equation

HRID 2113551 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.S(=O)(=O)=O.N1C=CC=CC=1.CO>ClCCl.CS(C)=O>[CH3:12][N:4]([CH2:3][CH:2]=[O:1])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateYield 57%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 2-hydroxyethyl(methyl)carbamate (24.52 g, 140 mmol) in 340 mL dichloromethane and 85 mL DMSO was added 39 mL (279.8 mmol) of triethylamine and the reaction mixture stirred at ambient temperature under N2. To this was added 45 g (280 mmol) of pyridine sulfur trioxide, portionwise. Exotherm was observed and the solution became clear dark yellow. Cooled to 0° C. and stirred for 1 hour 20 minutes. Monitored by TLC (10% methanol in dichloromethane). Concentrated to a total volume of ˜250 mL. Washed with 3×250 mL H2O then 250 mL NaCl (sat). Dried over MgSO4, filtered, and solvent evaporated. Distilled at 75° C. (3 mm Hg) to provide 13.83 g of a clear liquid.

Workup

  1. temperatureCooled to 0° C.
  2. stirringstirred for 1 hour 20 minutes
  3. concentrationConcentrated to a total volume of ˜250 mL
  4. washWashed with 3×250 mL H2O
  5. dry with materialDried over MgSO4
  6. filtrationfiltered
  7. customsolvent evaporated
  8. distillationDistilled at 75° C. (3 mm Hg)

Sources & evidence

ORD record
ord-f9c82db1b0844266970017650f4bcbd3
Source dataset
uspto-grants-2008_10
Patent number
US07432277B2

Reaction notes

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