(+/-)-(5Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-(tetrahydropyran-2-yloxy)-cyclopentyl}-5-heptenic acid methyl ester → (+/-)-(Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-hydroxy-cyclopentyl}-5-heptenic acid methyl ester heptenic acid methyl ester

HRID 1382532Notes

Reaction equation

HRID 1382532 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C@H:14]([Cl:15])[CH2:13][C@@H:12]([O:16]C2CCCCO2)[C@@H:11]1/[CH:23]=[CH:24]/[C:25](=[O:33])[C:26]([CH3:32])([CH3:31])[CH2:27][CH2:28][CH2:29][CH3:30]>C(O)(=O)C.O.O1CCCC1>[CH3:1][O:2][C:3](=[O:34])[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C@H:14]([Cl:15])[CH2:13][C@@H:12]([OH:16])[C@@H:11]1/[CH:23]=[CH:24]/[C:25](=[O:33])[C:26]([CH3:32])([CH3:31])[CH2:27][CH2:28][CH2:29][CH3:30]

Participants

3

Reactant 1

HCID 13853246(+/-)-(5Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-(tetrahydropyran-2-yloxy)-cyclopentyl}-5-heptenic acid methyl ester

Product 1

HCID 86742756(+/-)-(Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-hydroxy-cyclopentyl}-5-heptenic acid methyl ester heptenic acid methyl esterYield 128.9%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

1 g of VIII is stirred for 24 hours at 40° C. with 25 ml of a mixture of glacial acetic acid-water-tetrahydrofuran (65/35/10). It is concentrated by evaporation in a vacuum, chromatographed on silica gel with hexane/10-50% ethyl acetate, and 720 mg of IX is obtained as oil.

Workup

  1. concentrationIt is concentrated by evaporation in a vacuum
  2. customchromatographed on silica gel with hexane/10-50% ethyl acetate

Sources & evidence

ORD record
ord-c9026c1539974a9db72925e5f1267b41
Source dataset
uspto-grants-1989_02
Patent number
US04806668

Reaction notes

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