HCID 86745711, compound → HCID 86745712, compound

HRID 373252Notes

Reaction equation

HRID 373252 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]([CH2:16][CH2:17][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].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>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]([CH2:16][CH2:17][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

4

Reactant 2

HCID 86745711HCID 86745711, compoundHCID 131709961Jones' reagent

Product 1

HCID 86745712HCID 86745712, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(1S,2R,3R,5S)-7(E)-(4-Carboxybutylidene)-2-[4(RS)-fluoro-3(RS)-hydroxyoctyl]-3 -tetrahydropyranyloxybicyclo[3.3.0]octane (13) (0.184 g) was oxidized with Jones reagent between about -15° and -5° C. After stirring for 40 minutes, isopropyl alcohol (0.43 ml) was added, and the mixture was treated by a usual work-up. Obtained crude product was purified on column chromatography (hexane/ethyl acetate=15/1-10/1) using silica gel treated with an acid (CC-4: available from Mallineckrodt Co., Ltd.) to give (1S,2R,3R,5S)-7(E)-(4-carboxybutylidene)-2-[4(RS)-fluoro-3-oxooctyl]-3-tetrahydropyranyloxybicyclo[3.3.0]octane (14) as a colorless oily product. Yield: 0.072 g (40%)

Workup

  1. additionthe mixture was treated by a usual work-up
  2. customObtained crude product
  3. customwas purified on column chromatography (hexane/ethyl acetate=15/1-10/1)
  4. additiontreated with an acid (CC-4: available from Mallineckrodt Co., Ltd.)

Sources & evidence

ORD record
ord-7f5ffff8ac7c45269df2480c3a606a79
Source dataset
uspto-grants-1992_11
Patent number
US05162370

Reaction notes

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