Triethylamine → carbonic acid 4-(2,5-dimethyl-phenyl)-2-(1-methoxy-piperidin-4-ylmethyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester

HRID 1844664Notes

Reaction equation

HRID 1844664 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[C:15]1[C:16](=[O:30])[NH:17][CH:18]([CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([O:28][CH3:29])[CH2:24][CH2:23]2)[C:19]=1[OH:20].CCN(CC)CC>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:5]([O:4][C:2](=[O:3])[O:20][C:19]1[CH:18]([CH2:21][CH:22]2[CH2:23][CH2:24][N:25]([O:28][CH3:29])[CH2:26][CH2:27]2)[NH:17][C:16](=[O:30])[C:15]=1[C:9]1[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=1[CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 682992393-(2,5-Dimethyl-phenyl)-4-hydroxy-5-(1-methoxy-piperidin-4-ylmethyl)-1,5-dihydro-pyrrol-2-one

Product 1

HCID 68299269carbonic acid 4-(2,5-dimethyl-phenyl)-2-(1-methoxy-piperidin-4-ylmethyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl chloroformate (72 mg, 0.67 mmol) was added dropwise to a solution of 3-(2,5-dimethyl-phenyl)-4-hydroxy-5-(1-methoxy-piperidin-4-ylmethyl)-1,5-dihydro-pyrrol-2-one (220 mg, 0.67 mmol), Et3N (94 mg, 0.9 mmol) and DMAP (30 mg, 0.25 mmol) in 10 ml of THF at room temperature. The mixture was stirred for 30 min and concentrated to dryness in vacuo. The residue was purified by column chromatography on silica gel. Yield: 150 mg of carbonic acid 4-(2,5-dimethyl-phenyl)-2-(1-methoxy-piperidin-4-ylmethyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (title compound P1.1) as a gum.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-01fd87e9a9df45fa831fe88d62545864
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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