Cyclohexene → HCID 18600529, compound

HRID 1583927Notes

Reaction equation

HRID 1583927 reaction equation
[C:1]([O:4][CH2:5][C:6](=[O:30])[C@:7]1([OH:29])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C:21](=[CH:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[C:13](=[CH2:27])[CH2:12]3)[CH2:9][C@@H:8]1[CH3:28])(=[O:3])[CH3:2].C1CCCCC=1>[Pd]>[C:1]([O:4][CH2:5][C:6](=[O:30])[C@:7]1([OH:29])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C:21](=[CH:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[C@@H:13]([CH3:27])[CH2:12]3)[CH2:9][C@@H:8]1[CH3:28])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8079CyclohexeneHCID 18600527HCID 18600527, compound

Product 1

HCID 18600529HCID 18600529, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Analogously to Example 1(E), 1.4 g of 21-acetoxy-17α-hydroxy-16β-methyl-6-methylene-4,9(11)-pregnadiene-3,20-dione is hydrogenated with cyclohexene and palladium/active carbon, worked up, and purified, thus obtaining 830 mg of 21-acetoxy-17α-hydroxy-6α,16β-dimethyl-4,9(11)-pregnadiene-3,20-dione, mp 197°-199° C.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-a41b110227fd452fa38755150c5bcaa6
Source dataset
uspto-grants-1985_11
Patent number
US04555507

Reaction notes

Loading…