2,2,2-Trichloroethyl chloroformate → HCID 67531776, compound

HRID 1880209Notes

Reaction equation

HRID 1880209 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]([C:21]#[N:22])[CH2:9]1)C1C=CC=CC=1.ClC(OCC(Cl)(Cl)Cl)=O>CC#N>[Cl:20][C:15]1[CH:14]=[C:13]([CH:11]2[CH2:12][NH:8][CH2:9][CH:10]2[C:21]#[N:22])[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 67531796HCID 67531796, compound

Product 1

HCID 67531776HCID 67531776, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3SR,4RS)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carbonitrile (2.0 g, 6.6 mmol) dissolved in CH3CN (30 mL) was added 2,2,2-trichloroethyl chloroformate (1.22 mL, 9.91 mmol) and stirring was continued for 4 hours at RT. Volatiles were removed under vacuo, and the residue was dissolved in AcOH (25 mL) before a total of 1.20 g 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 the crude reaction product obtained used in the next reaction step, yielding 0.6 g (55%) of the title compound as a light yellow oil. ES-MS m/e: 242.1 (M+H+).

Workup

  1. customVolatiles were removed under vacuo
  2. dissolutionthe residue was dissolved in AcOH (25 mL) before a total of 1.20 g 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. customThe organic phases were dried on Na2SO4
  9. customthe crude reaction product
  10. customobtained
  11. customused in the next reaction step

Sources & evidence

ORD record
ord-0f56ad4c30874c54ac1078f2bfe28fca
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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