Water → HCID 22736936, compound

HRID 50861Notes

Reaction equation

HRID 50861 reaction equation
[F:1][C:2]1[C:11]([C:12](=[O:29])[CH2:13][N:14]2[CH2:19][CH2:18][C:17]([OH:28])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:30])[NH:7]2.[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[C:11]([CH:12]([OH:29])[CH2:13][N:14]2[CH2:15][CH2:16][C:17]([OH:28])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[CH2:18][CH2:19]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:30])[NH:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22736931HCID 22736931, compound

Product 1

HCID 22736936HCID 22736936, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 5-Fluoro-6-[[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]acetyl]-3,4-dihydroquinolin-2(1H)-one (630 mg, 1.5 mmol) and sodium borohydride (57 mg, 1.5 mmol) in ethanol (17 ml) was stirred at room temperature overnight. To the mixture was added water and extracted with dichloromethane. The extract was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (dichloromethane/methanol=10/1) to afford 5-Fluoro-6-[1-hydroxy-2-[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]ethyl]-3,4-dihydroquinolin-2(1H)-one as a yellow solid (220 mg).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-4a7666dd809b4aaeb833848863166315
Source dataset
uspto-grants-2004_03
Patent number
US06713490B2

Reaction notes

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