Tributylstannane → HCID 22813307, compound

HRID 1732214Notes

Reaction equation

I[C@@H:2]([C@@H:10]1[O:28][C@H:13]2[CH2:14][C@@H:15]([CH3:27])[C@@H:16](/[CH:17]=[CH:18]/[C@@H:19]([OH:26])[C@H:20]([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[C@H:12]2[CH2:11]1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>CCCCCC>[O:28]1[C@H:13]2[CH2:14][C@@H:15]([CH3:27])[C@@H:16](/[CH:17]=[CH:18]/[C@@H:19]([OH:26])[C@H:20]([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[C@H:12]2[CH2:11][C@@H:10]1[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1.0 g of [5R,6R,8R,9S,11R,12S,15R,16R]-methyl 5-iodo-6,9-epoxy-11-methyl-16-fluoro-15-hydroxyprost-(13E)-enoate in 50 ml of hexane was added 0.75 g of tri-n-butyltin hydride and a catalytic amount of 2,2'-azobis (2-methylpropionitrile). This solution was warmed to 50° C. for three hours after which the solvent was removed and the residual materials separated by silica gel chromatography to give 0.72 g of [6S,8R,9S,11R,12S,15R,16R]methyl 6,9-epoxy-11-methyl-16-fluoro-15-hydroxyprost-(13E)-enoate.

Workup

customwas removed
customthe residual materials separated by silica gel chromatography

Sources & evidence

ORD record: ord-38f4dbab354c401dab0de5501ba7e997
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04237060

Reaction notes

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