HCID 131717629, compound → HCID 18648699, compound

HRID 373249Notes

Reaction equation

HRID 373249 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH:7]=[CH:8][C:9]1[CH2:16][C@H:15]2[C@H:11]([CH2:12][C@@H:13]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[C@H:14]2/[CH:17]=[CH:18]/[C:19](=[O:26])[CH:20]([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:10]=1)=[O:4]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH2:16][C@H:15]2[C@H:11]([CH2:12][C@@H:13]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[C@@H:14]2[CH2:17][CH2:18][C:19](=[O:26])[CH:20]([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 131717629HCID 131717629, compound

Product 1

HCID 18648699HCID 18648699, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(1S,5S,6S,7R)-3-[4-Methoxycarbonyl-1(EZ)-butenyl]-6-[4(RS)-fluoro-3-oxo-(E )-1-octenyl]-7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene (5) (0.094 g) was dissolved in ethyl acetate. Into the solution, palladium(5 wt %)/carbon (0.0094 g) was added and the mixture was stirred under reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. Obtained crude product was chromatographed using a silica gel treated with silver nitrate (15 wt %) (hexane/ethyl acetate=12/1-9/1) to give (1S,5S,6R,7R)-3-(4-methoxycarbonyl)-6-[4(RS)-fluoro-3-oxooctyl]- 7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene (6) as a pale yellow oily product. Yield: 0.042 g (44%)

Workup

  1. filtrationwas filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customObtained crude product
  4. customwas chromatographed
  5. additiontreated with silver nitrate (15 wt %) (hexane/ethyl acetate=12/1-9/1)

Sources & evidence

ORD record
ord-34be20b33959484db719f338f043ace1
Source dataset
uspto-grants-1992_11
Patent number
US05162370

Reaction notes

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