(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid methyl ester → (5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-dihydroxyprostanoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH:7]([Br:26])[CH:8]1[O:25][C@H:11]2[CH2:12][C@@H:13]([OH:24])[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH:7]([Br:26])[CH:8]1[O:25][C@H:11]2[CH2:12][C@@H:13]([OH:24])[C@H:14]([CH2:15][CH2:16][C@@H:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
350 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid methyl ester (prepared as described in Example 2) were hydrogenated at a pressure of one atmosphere in 6 ml of ethanol containing 120 mg of 5% palladium on charcoal at room temperature. The reduction was stopped after the absorption of one equivalent of hydrogen. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:1) as eluent to give 210 mg of the title compound having the following physical characteristics:
Workup
- customThe catalyst was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel using
- additiona mixture of cyclohexane and ethyl acetate (1:1) as eluent
Sources & evidence
- ORD record
- ord-c065c92861cb4a57a89bd37bcf465c14
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04399147
Reaction notes
Loading…