HCID 86745713, compound → HCID 131717313, compound

HRID 373254Notes

Reaction equation

HRID 373254 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6]/[CH:7]=[C:8]1\[CH2:9][C@@H:10]2[C@H:14]([CH2:15]\1)[C@H:13](/[CH:16]=[CH:17]/[CH:18]([OH:25])[CH:19]([F:24])[CH2:20][CH2:21][CH2:22][CH3:23])[C@H:12]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:11]2)([OH:3])=[O:2]>C(O)(C)C>[C:1]([CH2:4][CH2:5][CH2:6]/[CH:7]=[C:8]1\[CH2:9][C@@H:10]2[C@H:14]([CH2:15]\1)[C@H:13](/[CH:16]=[CH:17]/[C:18](=[O:25])[CH:19]([F:24])[CH2:20][CH2:21][CH2:22][CH3:23])[C@H:12]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:11]2)([OH:3])=[O:2]

Participants

3

Reactant 1

HCID 86745713HCID 86745713, compound

Product 1

HCID 131717313HCID 131717313, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(1S,2S,3R,5S)-(E)-7-(4-Carboxybutylidene)-2-[4(RS)fluoro-3(RS)-hydroxy-(E)-1-octenyl]-3-tetrahydropyranyloxybicyclo[3.3.0]octane (13') (0.140 g) was subjected to Jones oxidation between -15 ° C. and -20 ° C. The mixture was stirred for 30 minutes, isopropyl alcohol was added to the mixture, and the resultant was treated by a usual work-up. The obtained crude product was purified on column chromatography (hexane/ethyl acetate=6/1-5/1) to give (1S,2S,3R,5S)-(E)-7-(4-carboxybutylidene)-2-[4(RS)-fluoro-3-oxo-(E)-1-octenyl]-3-tetrahydropyranyloxybicyclo[3.3.0]octane (14') as a colorless oily product. Yield: 0.106 g (76%)

Workup

  1. customwas subjected to Jones oxidation between -15 ° C. and -20 ° C
  2. additionthe resultant was treated by a usual work-up
  3. customThe obtained crude product
  4. customwas purified on column chromatography (hexane/ethyl acetate=6/1-5/1)

Sources & evidence

ORD record
ord-6a503b6d840740a8af3395b0965d88dc
Source dataset
uspto-grants-1992_11
Patent number
US05162370

Reaction notes

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