Triethylamine → 4-nitrophenyl (2S)-1,1,1-trifluoropropan-2-yl carbonate

HRID 872206Notes

Reaction equation

HRID 872206 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:14])([F:13])[C@@H:10]([OH:12])[CH3:11].Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:17]>CN(C)C1C=CN=CC=1.ClCCl>[F:8][C:9]([F:14])([F:13])[C@@H:10]([O:12][C:16](=[O:17])[O:18][C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)[CH3:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 6999971(2S)-1,1,1-Trifluoropropan-2-ol

Product 1

HCID 687562104-nitrophenyl (2S)-1,1,1-trifluoropropan-2-yl carbonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.3 mL) is added to a solution of 4-dimethylaminopyridine (13 mg), (S)-1,1,1-trifluoro-propan-2-ol (75% in tert-butyl methyl ether; 2.00 g), and 4-nitrophenyl chloroformate (2.90 g) in dichloromethane (80 mL) chilled in an ice bath. The solution is stirred in the cooling bath for 30 min and then at room temperature overnight. The solution is washed with 10% aqueous K2CO3 solution and water and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (dichloromethane) to give the title compound.

Workup

  1. temperaturechilled in an ice bath
  2. customat room temperature
  3. customovernight
  4. washThe solution is washed with 10% aqueous K2CO3 solution and water
  5. dry with materialdried (MgSO4)
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-caff9032d4db43b69739e4b24baae42a
Source dataset
uspto-grants-2015_03
Patent number
US08975277B2

Reaction notes

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