2,2,2-Trichloroethyl chloroformate → Rel-tert-butyl ((3R,4S)-4-(3,4-dichlorophenyl)pyrrolidin-3-yl)(methyl)carbamate

HRID 2066998Notes

Reaction equation

HRID 2066998 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH:9]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:12][N:11](CC2C=CC=CC=2)[CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(Cl)(Cl)Cl)=O>CC#N>[C:1]([O:5][C:6](=[O:29])[N:7]([C@@H:9]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:12][NH:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 67025859[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 58009331Rel-tert-butyl ((3R,4S)-4-(3,4-dichlorophenyl)pyrrolidin-3-yl)(methyl)carbamateYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of [(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (928 mg, 2.13 mmol) in CH3CN (10 ml) at RT, was added 2,2,2-trichloroethyl chloroformate (0.45 ml, 2.13 mmol). The reaction mixture was stirred at RT for 3 hours, concentrated under vacuo. The residue was dissolved in AcOH (5 ml) and zinc dust (400 mg) was added portion wise over 1 hours. The solvent was evaporated, the residue diluted in EtOAc and the organic phase was washed with an aqueous solution of NaHCO3. The organic phase was dried over Na2SO4 and concentrated under vacuo to afford 415 mg (98%) of the tile compound as a light yellow oil. ES-MS m/e: 345.2 (M+H+).

Workup

  1. concentrationconcentrated under vacuo
  2. dissolutionThe residue was dissolved in AcOH (5 ml)
  3. additionzinc dust (400 mg) was added portion wise over 1 hours
  4. customThe solvent was evaporated
  5. additionthe residue diluted in EtOAc
  6. washthe organic phase was washed with an aqueous solution of NaHCO3
  7. dry with materialThe organic phase was dried over Na2SO4
  8. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-4e41abf188d6459a8559ae69482c840c
Source dataset
uspto-grants-2012_10
Patent number
US08293770B2

Reaction notes

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