2-Aminomethyl-1,4-benzodioxane → 1-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

HRID 453842

Reaction equation

HRID 453842 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][NH2:12].[C:13]([O:22][CH3:23])(=[O:21])[C:14]([CH2:16][C:17](OC)=[O:18])=[CH2:15]>>[CH3:23][O:22][C:13]([CH:14]1[CH2:16][C:17](=[O:18])[N:12]([CH2:11][CH:2]2[O:1][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[O:4][CH2:3]2)[CH2:15]1)=[O:21]

Participants

3

Reactant 2

HCID 150532-Aminomethyl-1,4-benzodioxaneHCID 69240Dimethyl itaconate

Product 1

HCID 667272991-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

Procedure

The title compound was prepared using 200 mg (1.21 mmol) of 2,3-dihydro-benzo[1,4]dioxin-2-ylmethylamine and 0.17 mL (1.21 mmol) of dimethyl itaconate according to the procedure for substituted pyrrolidines described in J. Org. Chem. 26 (1961) 1519-1524. Purification by column chromatography (silica gel, heptane/ethyl acetate, 1:2) afforded the pure product.

Workup

  1. customPurification by column chromatography (silica gel, heptane/ethyl acetate, 1:2)
  2. customafforded the pure product

Sources & evidence

ORD record
ord-977d1ef380d045e5ad2058b45a2eef62
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Linked notes

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