Ethyl Acetate → 4-(2-Hydroxymethyl-1-pyrrolidinyl)-2-nitrobenzoic acid methyl ester

HRID 917613Notes

Reaction equation

HRID 917613 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].[NH:15]1[CH2:21][CH2:20][CH2:19][C@H:16]1[CH2:17][OH:18].CN1CCCC1=O.C(OCC)(=O)C>O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N:15]2[CH2:21][CH2:20][CH2:19][CH:16]2[CH2:17][OH:18])=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 39135Methyl 4-chloro-2-nitrobenzoateHCID 640091L-Prolinol

Product 1

HCID 692642464-(2-Hydroxymethyl-1-pyrrolidinyl)-2-nitrobenzoic acid methyl esterYield 15.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-nitrobenzoic acid methyl ester 100 mg, prolinol 235 mg and 1-methyl-2-pyrrolidinone 3 ml is stirred at 100° C. for 3 hours. After cooling to room temperature, ethyl acetate and water are added to the mixture. The organic layer is washed with water (twice) and brine, and dried over sodium sulfate. After removal of the sodium sulfate, the filtrate is concentrated in vacuo, and the residue is purified with preparative thin-layer chromatography (two plates, solvent; hexane:ethyl acetate=1:1) to give 4-(2-hydroxymethyl-1-pyrrolidinyl)-2-nitrobenzoic acid methyl ester 20 mg as a yellow oil. MS(m/z): 281 (M+H)+

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer is washed with water (twice) and brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the sodium sulfate
  5. concentrationthe filtrate is concentrated in vacuo
  6. customthe residue is purified with preparative thin-layer chromatography (two plates, solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-801b467decb5450e90f4949370879e16
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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