Hydrochloric Acid → HCID 68299225, compound

HRID 1844677Notes

Reaction equation

HRID 1844677 reaction equation
C[O:2][C:3](=O)[CH:4]([CH:18]1[CH2:23][CH2:22][N:21]([O:24][CH3:25])[CH2:20][CH2:19]1)[NH:5][C:6](=[O:17])[CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=1[CH3:16].CC([O-])(C)C.[K+].Cl>CN(C=O)C>[OH:2][C:3]1[CH:4]([CH:18]2[CH2:19][CH2:20][N:21]([O:24][CH3:25])[CH2:22][CH2:23]2)[NH:5][C:6](=[O:17])[C:7]=1[C:8]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=1[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 68299235HCID 68299235, compound

Product 1

HCID 68299225HCID 68299225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1-methoxy-piperidin-4-yl)-[2-(2,4,6-trimethyl-phenyl)-acetylamino]-acetic acid methyl ester (1.217 g, 3.36 mmol) in DMF (6 ml) at 90° C. under nitrogen was added t-BuOK (1.12 g, 10 mmol), the mixture was stirred for 10 min. Then the reaction mixture was poured into diluted hydrochloric acid and concentrated in vacuum. The crude product was purified by column chromatography on silica gel. Yield: 960 mg of 4-hydroxy-5-(1-methoxy-piperidin-4-yl)-3-(2,4,6-trimethyl-phenyl)-1,5-dihydro-pyrrol-2-one (compound P2.12) as a solid, mp 206-209° C.

Workup

  1. concentrationconcentrated in vacuum
  2. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-306eacffcdb64f4facbf34f764125fb7
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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