Toluene → tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate

HRID 546716Notes

Reaction equation

HRID 546716 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([OH:10])=[O:9].C1(C)C=CC=CC=1>CO>[CH3:1][O:9][C:8]([CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 167693TrimethylsilyldiazomethaneHCID 40183572-{1-[(Tert-butoxy)carbonyl]pyrrolidin-2-yl}acetic acid

Product 1

HCID 13425758tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethylsilyldiazomethane (2 M solution in hexane, 1.5 ml) was added dropwise to a mixed solution of tert-butyl 2-carboxymethylpyrrolidine-1-carboxylate (CAS No. 194154-91-1, 500 mg) in methanol (1 ml)-toluene (1 ml) under ice-cooling, and the reaction solution was stirred at the same temperature for three hours. The reaction solution was concentrated. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 506 mg of the title compound. The property values of the compound are as follows.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-7a8e9d1a2d204e72bf6ba8c9b0dff4bb
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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