1-Chloroethyl chloroformate → Methyl pyrrolidine-3-carboxylate hydrochloride

HRID 1454346Notes

Reaction equation

HRID 1454346 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9]1)C1C=CC=CC=1.[Cl:17]C(OC(Cl)C)=O>ClCCCl>[ClH:17].[NH:8]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 4610751Methyl 1-benzylpyrrolidine-3-carboxylate

Product 1

HCID 19261352Methyl pyrrolidine-3-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 0.52 g (2.3 mmol) of (R/S)-1-benzyl-pyrrolidin-3-yl carboxylic acid, methyl ester (from Step A) in 5 mL of 1,2-dichloroethane was treated with 0.3 mL (2.7 mmol) of 1-chloroethyl chloroformate (ACE-Cl). The resulting mixture was stirred at rt for 3 h, then at reflux for 30 min. The reaction was cooled and concentrated. The residue was warmed to reflux in 5 mL of MeOH for 1 h. The reaction was cooled and concentrated. The crude product was used in Step C without further purification.

Workup

  1. temperatureat reflux for 30 min
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. temperatureThe residue was warmed
  5. temperatureto reflux in 5 mL of MeOH for 1 h
  6. temperatureThe reaction was cooled
  7. concentrationconcentrated
  8. customThe crude product was used in Step C without further purification

Sources & evidence

ORD record
ord-df06876721094fbfb817f5f0b5b76575
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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