1-Chloroethyl chloroformate → 3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidine

HRID 874768Notes

Reaction equation

HRID 874768 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)([C:13]([F:16])([F:15])[F:14])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[Cl:23][C:21]1[CH:22]=[C:17]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:18]=[C:19]([Cl:24])[CH:20]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 58218883HCID 58218883, compound

Product 1

HCID 582188803-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidineYield 97.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The solution of 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (5.7 g) and 1-chloroethyl chloroformate (4.4 g) in dichloroethane was heated to reflux for 3 hours. The mixture was cooled to room temperature and then concentrated under the reduced pressure. Methanol was added to the resultant residue, which was then heated with stirring at 60° C. for two hours. The mixture was cooled to room temperature, to which was then added water. The solution was washed twice with the mixed solvent of hexane and ethyl acetate (9:1). The solution was alkalized with sodium hydrogen carbonate and then extracted with ethyl acetate three times. The organic layer was combined, which was then washed with brine and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure to yield 3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (4.2 g). 1H-NMR (CDCl3) δ: 2.24-2.33 (1H, m), 2.51-2.56 (1H, m), 2.97-3.07 (1H, m), 3.19-3.26 (2H, m), 3.74 (1H, d), 7.25 (2H, d), 7.35 (1H, t)

Workup

  1. temperatureto reflux for 3 hours
  2. concentrationconcentrated under the reduced pressure
  3. additionMethanol was added to the resultant residue, which
  4. temperaturewas then heated
  5. temperatureThe mixture was cooled to room temperature, to which
  6. washThe solution was washed twice with the mixed solvent of hexane and ethyl acetate (9:1)
  7. extractionextracted with ethyl acetate three times
  8. washwhich was then washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter the drying agent was filtered off
  11. distillationthe solvent was distilled away under the reduced pressure

Sources & evidence

ORD record
ord-1e5e4a0a91304ddb8cd68758de3959f3
Source dataset
uspto-grants-2015_03
Patent number
US08980937B2

Reaction notes

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