Hydrochloric Acid → 3-(2,5-Dimethyl-phenyl)-4-hydroxy-5-(1-methoxy-piperidin-4-ylmethyl)-1,5-dihydro-pyrrol-2-one

HRID 1844663Notes

Reaction equation

HRID 1844663 reaction equation
CC([O-])(C)C.[K+].C[O:8][C:9](=O)[CH:10]([NH:20][C:21](=[O:31])[CH2:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[CH3:30])[CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([O:18][CH3:19])[CH2:14][CH2:13]1.Cl>C1COCC1>[CH3:30][C:24]1[CH:25]=[CH:26][C:27]([CH3:29])=[CH:28][C:23]=1[C:22]1[C:21](=[O:31])[NH:20][CH:10]([CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([O:18][CH3:19])[CH2:16][CH2:17]2)[C:9]=1[OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 682992292-[2-(2,5-Dimethyl-phenyl)-acetylamino]-3-(1-methoxy-piperidin-4-yl)-propionic acid methyl ester

Product 1

HCID 682992393-(2,5-Dimethyl-phenyl)-4-hydroxy-5-(1-methoxy-piperidin-4-ylmethyl)-1,5-dihydro-pyrrol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, t-BuOK (1.8 g, 16.0 mmol) was added to a stirred solution of 2-[2-(2,5-dimethyl-phenyl)-acetylamino]-3-(1-methoxy-piperidin-4-yl)-propionic acid methyl ester (2.6 g, 8.0 mmol) in 15 ml of THF at 60° C. and the mixture was stirred at the same temperature for another 30 min. Then, the mixture was poured into diluted hydrochloric acid (50 ml) and extracted with ethyl acetate five times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash chromatography on silica gel. Yield: 500 mg of 3-(2,5-dimethyl-phenyl)-4-hydroxy-5-(1-methoxy-piperidin-4-ylmethyl)-1,5-dihydro-pyrrol-2-one (compound P2.2) as a solid, mp 116-119° C.

Workup

  1. extractionextracted with ethyl acetate five times
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-862dffc13f624e54a0a8a9cdcf4bc62e
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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