2,2,2-Trichloroethyl chloroformate → HCID 67131455, compound

HRID 906913Notes

Reaction equation

HRID 906913 reaction equation
C([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:10]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:9]1)C1C=CC=CC=1.ClC(OCC(Cl)(Cl)Cl)=O>CC#N>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH:10]2[CH:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[CH2:12][NH:8][CH2:9]2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 67131589HCID 67131589, compound

Product 1

HCID 67131455HCID 67131455, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3SR,4RS)-1-benzyl-3-(4-chloro-phenoxymethyl)-4-(3,4-dichloro-phenyl)-pyrrolidine 350 mg (0.78 mmol) dissolved in CH3CN (8 mL) was added 0.12 mL (0.86 mmol) of 2,2,2-trichloroethyl chloroformate and stirring was continued for 2 hours at RT. Volatiles were removed under vacuo, and the crude residue was dissolved in AcOH (5 mL) before a total of 200 mg of Zn dust was added portion wise. After three hours at RT, the reaction mixture was filtered on celite, the solvent removed under vacuo, followed by an extraction with EtOAc/aq. NaHCO3 (basic pH). The organic phases were dried on Na2SO4 and column chromatography (SiO2, CH2Cl2/MeOH 9:1 to 8:2) yielded 210 mg (75%) of the title compound as a colorless oil. ES-MS m/e: 357.1 (M+H+).

Workup

  1. customVolatiles were removed under vacuo
  2. dissolutionthe crude residue was dissolved in AcOH (5 mL) before a total of 200 mg of Zn dust
  3. additionwas added portion wise
  4. waitAfter three hours at RT
  5. filtrationthe reaction mixture was filtered on celite
  6. customthe solvent removed under vacuo
  7. extractionfollowed by an extraction with EtOAc/aq
  8. dry with materialThe organic phases were dried on Na2SO4 and column chromatography (SiO2, CH2Cl2/MeOH 9:1 to 8:2)

Sources & evidence

ORD record
ord-2896ff0060564c6e95a4ac8ca5431ec0
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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