Hydrochloric Acid → 6-{(E)-1-[3-Chloro-4-(methylsulfanyl)phenyl]-2-[(1S)-3-hydroxycyclopentyl]ethenyl}-3-cyclopropylpyridin-2(1H)-one

HRID 70601Notes

Reaction equation

HRID 70601 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6](/[C:12](/[C:20]2[NH:25][C:24](=[O:26])[C:23]([CH:27]3[CH2:29][CH2:28]3)=[CH:22][CH:21]=2)=[CH:13]\[C@H:14]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]2)[CH:7]=[CH:8][C:9]=1[S:10][CH3:11].Cl>C(O)C.O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6](/[C:12](/[C:20]2[NH:25][C:24](=[O:26])[C:23]([CH:27]3[CH2:29][CH2:28]3)=[CH:22][CH:21]=2)=[CH:13]\[C@H:14]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]2)[CH:7]=[CH:8][C:9]=1[S:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67398685HCID 67398685, compound

Product 1

HCID 584528136-{(E)-1-[3-Chloro-4-(methylsulfanyl)phenyl]-2-[(1S)-3-hydroxycyclopentyl]ethenyl}-3-cyclopropylpyridin-2(1H)-oneYield 69.6%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Sodium borohydride (11 mg) was added to a suspension of 6-{(E)-1-[3-chloro-4-(methylsulfanyl)phenyl]-2-[(1S)-3-oxocyclopentyl]ethenyl}-3-cyclopropylpyridin-2(1H)-one obtained in Example 1-71 (50 mg) in ethanol-tetrahydrofuran (2.5 mL, 4:1) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was poured into 0.5 M hydrochloric acid, followed by extraction with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give the title compound (35 mg, 60%) as a colorless amorphous.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

Sources & evidence

ORD record
ord-0d846df33488401789f3adf4739bf13b
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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