1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → (11beta)-21-(Acetyloxy)-11-hydroxypregna-1,4,16-triene-3,20-dione

HRID 1578025Notes

Reaction equation

HRID 1578025 reaction equation
C(O[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:32])[CH:22]=[CH:23]2)[CH2:18][CH2:17]3)[CH2:14][CH2:13]1)[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=O)C.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>>[C:9]([O:8][CH2:7][C:6](=[O:12])[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:32])[CH:22]=[CH:23]2)[CH2:18][CH2:17]3)[CH2:14][CH:13]=1)(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 14233395Prednisolone 17,21-diacetate

Product 1

HCID 102365(11beta)-21-(Acetyloxy)-11-hydroxypregna-1,4,16-triene-3,20-dioneYield 81%

Procedure

One gram of 17α,21-diacetoxy-11β-hydroxy-1,4- pregnadiene-3,20-dione is treated analogously to Example 1 in "Dowtherm" for 50 minutes at 250° C. and worked up. Recrystallization from isopropyl ether yields 700 mg of 21-acetoxy-11β-hydroxy-1,4,16-pregnatriene-3,20-dione (81% of theory).

Workup

  1. customRecrystallization from isopropyl ether

Sources & evidence

ORD record
ord-3f6fb4f1f2ab440592833401d2ffe519
Source dataset
uspto-grants-1981_09
Patent number
US04290963

Reaction notes

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