Benzyl chloroformate → Diethyl (1-benzyloxycarbonyl-3-azetidinyl)malonate

HRID 1457996Notes

Reaction equation

HRID 1457996 reaction equation
C([N:14]1[CH2:17][CH:16]([CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>ClCCl>[CH2:33]([O:32][C:30]([N:14]1[CH2:17][CH:16]([CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15]1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 11132697Diethyl (1-benzhydryl-3-azetidinyl)malonate

Product 1

HCID 54152329Diethyl (1-benzyloxycarbonyl-3-azetidinyl)malonateYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3.40 g (8.91 mmol) of diethyl (1-benzhydryl-3-azetidinyl)malonate dissolved in 30 ml of dichloromethane was added 1.91 ml (13.36 mmol) of benzyl chloroformate, followed by overnight stirring at room temperature. After evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (250 ml, 3-5% methanol-dichloromethane) to yield 2.64 g (84%) of the title compound.

Workup

  1. customAfter evaporation of the solvent
  2. customthe resulting residue was purified by a silica gel column chromatography (250 ml, 3-5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-d816966daaa64be2a1fa8a7406440e52
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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