Tributylstannane → HCID 70363829, compound

HRID 1583930Notes

Reaction equation

[C:1]([O:4][C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@:26](Br)([C@@H:27]([OH:31])[CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:33])[CH:22]=[CH:23]2)[C@@H:18]([CH3:34])[CH2:17]3)[CH2:14][C@@H:13]1[CH3:35])[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].C([SnH](CCCC)CCCC)CCC>>[C:1]([O:4][C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([C@@H:27]([OH:31])[CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:33])[CH:22]=[CH:23]2)[C@@H:18]([CH3:34])[CH2:17]3)[CH2:14][C@@H:13]1[CH3:35])[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 5948Tributylstannane

HCID 70447438HCID 70447438, compound

Product 1

HCID 70363829HCID 70363829, compoundYield 101.5%

Procedure

As described in Example 1(G), 460 mg of 17α,21-diacetoxy-9α-bromo-11β-hydroxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione is debrominated with tributyltin hydride and worked up, thus obtaining 400 mg of 17α,21-diacetoxy-11β-hydroxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione, mp 124°-126° C.

Sources & evidence

ORD record: ord-33f99deb417a4329a8f7ce541c4befd4
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04555507

Reaction notes

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