(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 553853Notes

Reaction equation

HRID 553853 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]>CO.[Pt]=O>[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 solution of (3S,8aR)-3-(3,4,5-trifluorophenyl)-2,3,6,8a-tetrahydro-1H-indolizin-5-one (680 mg) in methanol (20 mL), and the reaction solution was stirred in a hydrogen atmosphere at 1 atm at room temperature for 2.5 hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure to obtain 684 mg of the title compound. The property value of the compound is as follows.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-003f6168e11441f790549584af27c486
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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