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

HRID 434735Notes

Reaction equation

HRID 434735 reaction equation
[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

Participants

6

Reactant 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

Product 1

HCID 86738982(13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl esterYield 92.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-dba6c7d395a74b92b8c50d5644d480a6
Source dataset
uspto-grants-1983_08
Patent number
US04399147

Reaction notes

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