16alpha-Hydroxyprednisolone → 11beta,17,21-Trihydroxy-16alpha-(2-phenyl-2-propenyloxy)-pregna-1,4-diene-3,20-dione

HRID 918407Notes

Reaction equation

HRID 918407 reaction equation
[N+](=[CH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:5])=[N-].[OH:12][C@H:13]1[CH2:33][C@@:32]2([CH3:34])[C@@H:24]([CH2:25][C@@H:26]([OH:36])[C@:27]2([OH:35])[C:28](=[O:31])[CH2:29][OH:30])[C@H:23]2[C@H:14]1[C@:15]1([CH3:38])[C:20]([CH2:21][CH2:22]2)=[CH:19][C:18](=[O:37])[CH:17]=[CH:16]1>>[OH:12][C@H:13]1[CH2:33][C@@:32]2([CH3:34])[C@@H:24]([CH2:25][C@@H:26]([O:36][CH2:5][C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH2:3])[C@:27]2([OH:35])[C:28](=[O:31])[CH2:29][OH:30])[C@H:23]2[C@H:14]1[C@:15]1([CH3:38])[C:20]([CH2:21][CH2:22]2)=[CH:19][C:18](=[O:37])[CH:17]=[CH:16]1

Participants

3

Reactant 2

HCID 1104705616alpha-HydroxyprednisoloneHCID 21520875(3-Diazoprop-1-en-2-yl)benzene

Product 1

HCID 6814240511beta,17,21-Trihydroxy-16alpha-(2-phenyl-2-propenyloxy)-pregna-1,4-diene-3,20-dione

Procedure

A solution of 1-diazo-2-phenyl-2-propene (prepared from 0.3 mole of N-nitrosourethane precursor) in methanolether at 0° is treated with 11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, 16,17-cycloborate (84 mmoles) until nitrogen evolution ceases. Solvent removal gives the title compound.

Workup

  1. customSolvent removal

Sources & evidence

ORD record
ord-2f60fa2f69f54321895e974f942ef05a
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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