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

HRID 918418Notes

Reaction equation

HRID 918418 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH:5]=[N+]=[N-])[CH3:2].[OH:11][C@H:12]1[CH2:32][C@@:31]2([CH3:33])[C@@H:23]([CH2:24][C@@H:25]([OH:35])[C@:26]2([OH:34])[C:27](=[O:30])[CH2:28][OH:29])[C@H:22]2[C@H:13]1[C@:14]1([CH3:38])[C:19]([C@@H:20]([CH3:36])[CH2:21]2)=[CH:18][C:17](=[O:37])[CH:16]=[CH:15]1>>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][O:35][C@@H:25]1[CH2:24][C@@H:23]2[C@:31]([CH3:33])([CH2:32][C@H:12]([OH:11])[C@H:13]3[C@H:22]2[CH2:21][C@H:20]([CH3:36])[C:19]2[C@:14]3([CH3:38])[CH:15]=[CH:16][C:17](=[O:37])[CH:18]=2)[C@@:26]1([OH:34])[C:27](=[O:30])[CH2:28][OH:29])[CH3:2]

Participants

3

Reactant 2

HCID 21520892Ethane, 2-diazo-1,1-diethoxy-HCID 6812909911beta,16alpha,17,21-Tetrahydroxy-6alpha-methylpregna-1,4-diene-3,20-dione

Product 1

HCID 2279178016alpha-[(2,2-Diethoxy)ethoxy]-11beta,17,21-trihydroxy-6alpha-methylpregna-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 11β,16α,17,21-tetrahydroxy-6α-methylpregna-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-7f21642a8a214e3e94911cc69ec1c3ab
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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