HCID 10979461, compound → HCID 11023011, compound

HRID 600893Notes

Reaction equation

HRID 600893 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=[O:22])[CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(OCC)(=O)C.[C].[Pt]>[CH2:1]([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH3:15])[C:11](=[O:22])[CH2:10]2)[CH2:7][CH2:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 10979461HCID 10979461, compound

Product 1

HCID 11023011HCID 11023011, compound

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

4-(1-ethoxycarbonylcyclopropyl)-1-[1-(S)-phenylethyl]-3-pyrrolin-2-one (12.1 g, 40.5 mmol) was dissolved in ethyl acetate (120 ml), a 5% platinum carbon catalyst (water content: 50%, 2.4 g) was added thereto, and it was stirred at room temperature for 17 hours under a hydrogen atmosphere at atmospheric pressure. The reaction solution was then filtered through cellite (washed with ethyl acetate) and the filtrate was then concentrated under a reduced pressure. The concentrate was applied to a silica gel chromatography, and 9.00 g (74%) of the compound of the title were obtained as a pale-yellow syrup from an n-hexane:ethyl acetate=3:2 eluate. Further, 2.60 g (21%) of the diastereomer (4-(R)-isomer) of the title compound was obtained as a pale-yellow syrup. The instrumental analysis data for this resulting compound agreed with the data indicated in PCT/JP96/00208.

Workup

  1. filtrationThe reaction solution was then filtered through cellite (washed with ethyl acetate)
  2. concentrationthe filtrate was then concentrated under a reduced pressure
  3. customwere obtained as a pale-yellow syrup from an n-hexane

Sources & evidence

ORD record
ord-f191adf8ac9c445a894e69928a4e46c8
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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