Benzyl chloroformate → HCID 68861769, compound

HRID 229505Notes

Reaction equation

HRID 229505 reaction equation
C([N:8]1[CH2:12][C@H:11]([CH3:13])[C@@:10]([CH3:19])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]1)C1C=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:8]1[CH2:12][C@H:11]([CH3:13])[C@@:10]([CH3:19])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformate2×HCID 68860907HCID 68860907, compound

Product 1

HCID 68861769HCID 68861769, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl(3R*,4R*)-1-benzyl-3,4-dimethylpyrrolidine-3-carboxylate (2.75 g, 10.0 mmol) in dichloromethane (30 mL), benzyl chloroformate (2.14 mL, 15.0 mmol) was added at room temperature, and the mixture was stirred at room temperature for 6 hours. Benzyl chloroformate (2.14 mL, 15.0 mmol) was also added to the mixture, and the mixture was stirred at room temperature for another 14 hours. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 9:1→4:1→2:1) to obtain 1.64 g of the title compound (5.37 mmol, 2 steps, 54%) as a colorless transparent oil.

Workup

  1. stirringthe mixture was stirred at room temperature for another 14 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 9:1→4:1→2:1)

Sources & evidence

ORD record
ord-e96816ae66404a299dd88dcd0b39afe7
Source dataset
uspto-grants-2009_07
Patent number
US07563805B2

Reaction notes

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