Benzyl chloroformate → HCID 53928292, compound

HRID 1457977Notes

Reaction equation

HRID 1457977 reaction equation
C1([C@H]([N:9]2[CH2:13][CH2:12][C@H:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]2)C)C=CC=CC=1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>ClCCl>[CH2:24]([O:23][C:21]([N:9]1[CH2:13][CH2:12][C@H:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 14975361HCID 14975361, compound

Product 1

HCID 53928292HCID 53928292, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 12 g (45.9 mmol) portion of (3R)-ethyl 1-[(R)-1-phenylethyl]pyrrolidine-3-acetate known in literatures was dissolved in 100 ml of dichloromethane to which was subsequently added dropwise 7.87 ml (55.1 mmol) of benzyl chloroformate at room temperature. After completion of the dropwise addition, the mixture was stirred for 16 hours at the same temperature. After completion of the reaction, the reaction mixture was concentrated. Thereafter, the resulting residue was applied to a silica gel column chromatography to yield 10.1 g (76%) of the title compound as an oily substance from the eluate of n-hexane:ethyl acetate=5:1.

Workup

  1. additionAfter completion of the dropwise addition
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-e3b3f3c89b18410fb6d841a49dadec4a
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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