3,4-dihydro-2H-pyran → 21-Tetrahydropyranyl-16alpha-cyano-11beta-hydroxy-3,20-dioxo-1,4-pregnadiene

HRID 34723Notes

Reaction equation

HRID 34723 reaction equation
[C:1]([C@@H:3]1[CH2:23][C@@H:22]2[C@:9]([CH3:27])([CH2:10][C@H:11]([OH:26])[C@H:12]3[C@H:21]2[CH2:20][CH2:19][C:18]2[C@:13]3([CH3:25])[CH:14]=[CH:15][C:16](=[O:24])[CH:17]=2)[C@H:4]1[C:5](=[O:8])[CH2:6]O)#[N:2].[O:28]1[CH:33]=[CH:32][CH2:31][CH2:30][CH2:29]1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[O:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[CH2:6][C:5](=[O:8])[C@@H:4]1[C@:9]2([CH3:27])[C@H:22]([C@H:21]3[C@H:12]([C@@H:11]([OH:26])[CH2:10]2)[C@:13]2([CH3:25])[C:18](=[CH:17][C:16](=[O:24])[CH:15]=[CH:14]2)[CH2:19][CH2:20]3)[CH2:23][C@H:3]1[C:1]#[N:2]

Participants

4

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 1423340516alpha-Cyano-11beta,21-dihydroxy-3,20-dioxo-1,4-pregnadiene

Product 1

HCID 2283930421-Tetrahydropyranyl-16alpha-cyano-11beta-hydroxy-3,20-dioxo-1,4-pregnadiene

Procedure

The process of claim 9 which additionally comprises reacting (VI) with 2,3-dihydropyran and pyridinium tosylate to produce (VII) 21-tetrahydropyranyl-16α-cyano-11β-hydroxy-3,20-dioxo-1,4-pregnadiene.

Sources & evidence

ORD record
ord-03b553c320894322b5171b838209cce9
Source dataset
uspto-grants-1988_08
Patent number
US04762919

Reaction notes

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