HCID 131717632, compound → HCID 86745716, compound

HRID 373256Notes

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:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[C@H:14]2/[CH:17]=[CH:18]/[CH:19]([OH:27])[C:20]([F:26])([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:10]=1)=[O:4]>CC(C)=O>[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9]1\[CH2:10][C@@H:11]2[C@H:15]([CH2:16]\1)[C@H:14](/[CH:17]=[CH:18]/[CH:19]([OH:27])[C:20]([F:26])([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[C@H:13]([O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1)[CH2:12]2)=[O:4]

Participants

Conditions

Temperature: 120 °C

Procedure

(1S,5S,6S,7R)-3-[4-Methoxycarbonyl-1(EZ)-butenyl]-6-[4,4-difluoro-3(RS) hydroxy-(E)-1-octenyl]-7-tetrahydropyranyloxybicyclo[3.3.0]oct-2ene (17) (0.184 g) was dissolved in acetone and the solution was placed in an autoclave, into which tricarbonyl chromium/methyl benzoate complex (0.021 g) was added, and then the autoclave was degassed. The mixture in the autoclave was stirred under hydrogen pressure (70 kg/cm2) at 120° C. for 15 hours. The reaction mixture was concentrated under reduced pressure, and the obtained crude product was purified on column chromatography (hexane/ethyl acetate=7/2-3/1) to give (1S,2S,3R,5S)-(E)-7-(4-methoxycarbonylbutylidene)-2-[4,4-difluoro-3(RS)-hydroxy-(E) -1-octenyl]-3-tetrahydropyranyloxybicyclo[3.3.0]octane (18) as a colorless oily product. Yield: 0.175 g (95%)

Workup

additionwas added
customthe autoclave was degassed
concentrationThe reaction mixture was concentrated under reduced pressure
customthe obtained crude product
customwas purified on column chromatography (hexane/ethyl acetate=7/2-3/1)

Sources & evidence

ORD record: ord-38c96ce89bec45a1aa99c672f112953f
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162370

Reaction notes

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