Benzyl chloroformate → 1-Benzyl 3-(4-methoxyphenyl)methyl (3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate

HRID 446012Notes

Reaction equation

HRID 446012 reaction equation
C([N:8]1[CH2:12][CH:11]([CH3:13])[C:10]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[O:15])[CH2:9]1)C1C=CC=CC=1.Cl[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]>ClCCl>[C:30]([O:29][C:27](=[O:28])[CH2:26][C:10]1([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[O:15])[CH:11]([CH3:13])[CH2:12][N:8]([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:36])[CH2:9]1)([CH3:33])([CH3:31])[CH3:32]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 86678246(4-methoxyphenyl)methyl (3RS,4SR)-1-benzyl-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-3-carboxylate

Product 1

HCID 780519391-Benzyl 3-(4-methoxyphenyl)methyl (3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylateYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (4-methoxyphenyl)methyl (3RS,4SR)-1-benzyl-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-3-carboxylate obtained in Example 2g (18 g, 39.7 mmol) in dichloromethane (85.7 ml) was adjusted to an internal temperature of 10 to 20° C., and benzyl chloroformate (11.9 ml, 79.4 mmol) was added thereto. After returning to mom temperature and stirring for 0.5 hour, the reaction mixture was concentrated directly. The resulting crude product was purified by column chromatography (silica gel, elution solvent: ethyl acetate/heptane) to give the title compound (12.89 g, yield: 65.3%).

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated directly
  3. customThe resulting crude product was purified by column chromatography (silica gel, elution solvent: ethyl acetate/heptane)

Sources & evidence

ORD record
ord-47451993a6b24fcd815aa4ebe433649c
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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