Ethane, 2-diazo-1,1-diethoxy- → 6alpha-Fluoro-16alpha-[(2,2-diethoxy)ethoxy]-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

HRID 918404Notes

Reaction equation

HRID 918404 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH:5]=[N+]=[N-])[CH3:2].[F:11][C@@H:12]1[C:32]2[C@:27]([CH3:34])([CH:28]=[CH:29][C:30](=[O:33])[CH:31]=2)[C@@H:26]2[C@H:14]([C@H:15]3[C@:23]([CH3:36])([CH2:24][C@@H:25]2[OH:35])[C@@:18]([OH:37])([C:19](=[O:22])[CH2:20][OH:21])[C@H:17]([OH:38])[CH2:16]3)[CH2:13]1>>[F:11][C@@H:12]1[C:32]2[C@:27]([CH3:34])([CH:28]=[CH:29][C:30](=[O:33])[CH:31]=2)[C@@H:26]2[C@H:14]([C@H:15]3[C@:23]([CH3:36])([CH2:24][C@@H:25]2[OH:35])[C@@:18]([OH:37])([C:19](=[O:22])[CH2:20][OH:21])[C@H:17]([O:38][CH2:5][CH:4]([O:8][CH2:9][CH3:10])[O:3][CH2:1][CH3:2])[CH2:16]3)[CH2:13]1

Participants

3

Reactant 2

HCID 21520892Ethane, 2-diazo-1,1-diethoxy-HCID 227932296alpha-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione

Product 1

HCID 227917836alpha-Fluoro-16alpha-[(2,2-diethoxy)ethoxy]-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

Procedure

A solution of 2,2-diethoxy-1-diazoethane (prepared from 0.18 mole of precursor as described in Example 2A) in methanolether at 0°C is treated with 6α-fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, 16,17-cycloborate until nitrogen evolution ceases. The solution is evaporated to give the title compound.

Workup

  1. customThe solution is evaporated

Sources & evidence

ORD record
ord-ce729fb729ad438ca1ac2e3c7d45e9a4
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

Loading…