Tributylstannane → (13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

HRID 434735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 434735
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH:7](Br)[CH:8]1[O:37][C@H:11]2[CH2:12][C@@H:13]([O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1.C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[O:37][C@H:11]2[CH2:12][C@@H:13]([O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1

Komponenten

6

Edukt 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 10340Sodium CarbonateHCID 86737122(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

Produkt 1

HCID 86738982(13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl esterAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

In a Pyrex (registered Trade Mark) vessel, a solution of 540 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Example 1), 322 mg of tri-n-butyl-tinhydride and 24 mg of 2,2'-azobisisobutyronitrile in 6 ml of benzene was irradiated with light from a high pressure mercury lamp at room temperature for 30 minutes. To the reaction mixture was added an aqueous sodium carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with water and aqueous sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (4:1) as eluent to give 435 mg of the title compound having the following physical characteristics:

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of cyclohexane and ethyl acetate (4:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-dba6c7d395a74b92b8c50d5644d480a6
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04399147

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