Tributylstannane → HCID 70363764, compound

HRID 256155Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6](=[O:36])[C@:7]1([O:31][CH2:32][O:33][CH2:34][CH3:35])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21](Br)([C@@H:22]([OH:26])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:28])[CH:17]=[CH:18]2)[C@@H:13]([CH3:29])[CH2:12]3)[CH2:9][C@@H:8]1[CH3:30])(=[O:3])[CH3:2].C([SnH](CCCC)CCCC)CCC>>[C:1]([O:4][CH2:5][C:6](=[O:36])[C@:7]1([O:31][CH2:32][O:33][CH2:34][CH3:35])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C@@H:22]([OH:26])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:28])[CH:17]=[CH:18]2)[C@@H:13]([CH3:29])[CH2:12]3)[CH2:9][C@@H:8]1[CH3:30])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 5948Tributylstannane

HCID 70363791HCID 70363791, compound

Product 1

HCID 70363764HCID 70363764, compoundYield 68.6%

Procedure

Analogously to Example 1(G), 2.2 g of 21-acetoxy-9α-bromo-17α-ethoxymethoxy-11β-hydroxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione is dehalogenated with tributyltin hydride, worked up, and purified, thus obtaining 1.3 g of 21-acetoxy-17α-ethoxymethoxy-11β-hydroxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione, mp 137°-139° C.

Workup

custompurified

Sources & evidence

ORD record: ord-ec873fde8dac460f9e9641fd953a267a
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04701451

Reaction notes

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