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1-Chloroethyl chloroformate → methyl (3R*,4S*)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate monohydrochloride

HRID 2047439
Notes
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Reaction equation

HRID 2047439 reaction equation
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[C@@H:10]([C:21]([O:23][CH3:24])=[O:22])[CH2:9]1)C1C=CC=CC=1.CC(Cl)OC(Cl)=O>C(#N)C>[ClH:19].[Cl:20][C:15]1[CH:14]=[C:13]([C@H:11]2[CH2:12][NH:8][CH2:9][C@@H:10]2[C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][C:16]=1[Cl:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 67232866methyl (3R*,4S*)-1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

Product 1

HCID 67232915methyl (3R*,4S*)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate monohydrochlorideYield 188.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the compound (33.4 g) obtained in step 2 in acetonitrile (250 mL) was added ACE-Cl (13.9 g) at room temperature, and the mixture was stirred at 90° C. for 2 hr. The reaction solution was cooled, and the solvent was evaporated under reduced pressure. To the residue was added methanol (250 mL), and the mixture was stirred at 80° C. for 2 hr. The reaction solution was cooled, the solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate/IPE to give methyl (3R*,4S*)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate monohydrochloride (26.9 g, 98%) as a pale-yellow powder.

Workup

  1. temperatureThe reaction solution was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the residue was added methanol (250 mL)
  4. stirringthe mixture was stirred at 80° C. for 2 hr
  5. temperatureThe reaction solution was cooled
  6. customthe solvent was evaporated under reduced pressure
  7. washthe residue was washed with ethyl acetate/IPE

Sources & evidence

ORD record
ord-07ae5e7febea407397f4f809797c8df5
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592454B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes