(3S,8aR)-3-(3,4,5-trifluorophenyl)-2,3,6,8a-tetrahydro-1H-indolizin-5-one → (3S,8aR)-3-(3,4,5-trifluorophenyl)hexahydroindolizin-5-one

HRID 16338Notes

Reaction equation

HRID 16338 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[N:18]3[C@@H:13]([CH:14]=[CH:15][CH2:16][C:17]3=[O:19])[CH2:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[H][H]>[Pt]=O.CO>[F:9][C:6]1[CH:5]=[C:4]([C@H:10]2[N:18]3[C@H:13]([CH2:14][CH2:15][CH2:16][C:17]3=[O:19])[CH2:12][CH2:11]2)[CH:3]=[C:2]([F:1])[C:7]=1[F:8]

Participants

5

Reactant 2

HCID 67466164(3S,8aR)-3-(3,4,5-trifluorophenyl)-2,3,6,8a-tetrahydro-1H-indolizin-5-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 67459901(3S,8aR)-3-(3,4,5-trifluorophenyl)hexahydroindolizin-5-oneYield 99.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Platinum oxide (100 mg) was added to a methanol solution (20 mL) of (3S,8aR)-3-(3,4,5-trifluorophenyl)-2,3,6,8a-tetrahydro-1H-indolizin-5-one (680 mg). The resulting reaction solution was stirred under 1 atm of hydrogen atmosphere at room temperature for 2.5 hr. The reaction solution was filtered through Celite. The filtrate was concentrated under reduced pressure to give 684 mg of the title compound. The physical property values of this compound were as follows:

Workup

  1. customThe resulting reaction solution
  2. filtrationThe reaction solution was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1ff13d7652504346b34c5557eebcdf22
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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