1-Chloroethyl chloroformate → HCID 67217912, compound

HRID 910454Notes

Reaction equation

HRID 910454 reaction equation
[C:1]([O:5][C:6](=[O:28])[N:7]([CH:9]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:12][N:11](CC2C=CC=CC=2)[CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].ClC(OC(Cl)C)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:28])[N:7]([CH:9]1[CH:13]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:12][NH:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 67025617HCID 67025617, compound

Product 1

HCID 67217912HCID 67217912, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of [(3RS,4SR)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (1.30 g, 3.20 mmol) in toluene (30 ml) at RT, was added 1-chloroethyl chloroformate (0.53 ml, 4.80 mmol). The reaction mixture was stirred at 90° C. overnight and concentrated under vacuo. The residue was dissolved in MeOH (30 ml) and the reaction mixture was heated at 80° C. for 2 hours. The solvent was evaporated and the crude product was directly used in the next step without further purification.

Workup

  1. concentrationconcentrated under vacuo
  2. dissolutionThe residue was dissolved in MeOH (30 ml)
  3. temperaturethe reaction mixture was heated at 80° C. for 2 hours
  4. customThe solvent was evaporated
  5. customthe crude product was directly used in the next step without further purification

Sources & evidence

ORD record
ord-0e3b620f32434c4cb175d41438b1c250
Source dataset
uspto-grants-2011_09
Patent number
US08022099B2

Reaction notes

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