Triethylamine → HCID 68299268, compound

HRID 1844678Notes

Reaction equation

HRID 1844678 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[OH:7][C:8]1[CH:12]([CH:13]2[CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]2)[NH:11][C:10](=[O:21])[C:9]=1[C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=1[CH3:30].CCN(CC)CC>CN(C1C=CN=CC=1)C.CC(C)=O>[CH3:20][O:19][N:16]1[CH2:17][CH2:18][CH:13]([CH:12]2[C:8]([O:7][C:2](=[O:3])[O:4][CH2:5][CH3:6])=[C:9]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[CH3:30])[C:10](=[O:21])[NH:11]2)[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 68299225HCID 68299225, compound

Product 1

HCID 68299268HCID 68299268, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolvent

Procedure

Ethyl chloroformate (216 mg, 2 mmol) was added dropwise to a mixture of 4-hydroxy-5-(1-methoxy-piperidin-4-yl)-3-(2,4,6-trimethyl-phenyl)-1,5-dihydro-pyrrol-2-one (400 mg, 1.2 mmol), Et3N (606 mg, 6 mmol) and DMAP (60 mg, 0.5 mmol) in acetone (20 ml). The mixture was stirred for 15 min and concentrated under vacuum to dryness. The residue was purified by column chromatography on silica gel. Yield: 260 mg of carbonic acid ethyl ester 2-(1-methoxy-piperidin-4-yl)-5-oxo-4-(2,4,6-trimethyl-phenyl)-2,5-dihydro-1H-pyrrol-3-yl ester (title compound P1.12) as a solid, mp 154-155° C.

Workup

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

Sources & evidence

ORD record
ord-a6c28041eb514bf794f52d9ee8b99fcb
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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