HCID 10734746, compound → HCID 12018318, compound

HRID 1635564Notes

Reaction equation

HRID 1635564 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([CH2:18][OH:19])([CH2:16][OH:17])[CH2:14][CH2:13][C:12]2=[O:20])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1)=[O:4]>C(OC(=O)C)(=O)C.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([CH2:18][O:19][C:16](=[O:17])[CH3:15])([CH2:16][O:17][C:3](=[O:2])[CH3:5])[CH2:14][CH2:13][C:12]2=[O:20])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 10734746HCID 10734746, compound

Product 1

HCID 12018318HCID 12018318, compoundYield 197.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 1-[4-methoxycarbonyl-2-(nitro)phenyl]-5,5-bis(hydroxymethyl)-pyrrolidin-2-one (500 mg, 1.54 mmol) from example 6 in acetic anhydride (0.5 mL) was treated with DMAP (15 mg) and the resulting mixture was stirred at room temperature for 1.5 h. The reaction mixture was dried under high vacuum and the resulting crude oil was purified by flash chromatography (silica gel; 10% ethanol in ether) to give 620 mg (98.5%) of 1-[4-methoxycarbonyl-2-(nitro)phenyl]-5,5-bis(acetyloxymethyl)pyrrolidin-2-one as an oil which solidified upon standing, mp, 61-63° C.

Workup

  1. customThe reaction mixture was dried under high vacuum
  2. customthe resulting crude oil was purified by flash chromatography (silica gel; 10% ethanol in ether)

Sources & evidence

ORD record
ord-ec9bfccd78394311bc2bb6404dbee1e7
Source dataset
uspto-grants-2003_01
Patent number
US06509359B1

Reaction notes

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