11beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dione → 16alpha-Allyloxy-11beta,17,21-trihydroxypregn-4-ene-3,20-dione

HRID 918412Notes

Reaction equation

HRID 918412 reaction equation
[OH:1][C@H:2]1[CH2:22][C@@:21]2([CH3:23])[C@@H:13]([CH2:14][C@@H:15]([OH:25])[C@:16]2([OH:24])[C:17](=[O:20])[CH2:18][OH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:27])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:26])[CH2:6][CH2:5]1.[CH:28]([CH:30]=[N+]=[N-])=[CH2:29]>>[CH2:30]([O:25][C@@H:15]1[CH2:14][C@@H:13]2[C@:21]([CH3:23])([CH2:22][C@H:2]([OH:1])[C@H:3]3[C@H:12]2[CH2:11][CH2:10][C:9]2[C@:4]3([CH3:27])[CH2:5][CH2:6][C:7](=[O:26])[CH:8]=2)[C@@:16]1([OH:24])[C:17](=[O:20])[CH2:18][OH:19])[CH:28]=[CH2:29]

Participants

3

Reactant 2

HCID 10200311beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dioneHCID 109094791-Diazo-2-propene

Product 1

HCID 6814270016alpha-Allyloxy-11beta,17,21-trihydroxypregn-4-ene-3,20-dione

Procedure

11β,16α,17,21-Tetrahydroxypregn-4-ene-3,20-dione, 16,17-cycloborate is added to a solution of vinyl diazomethane in 1:1 methanol-ether at 0°C until nitrogen evolution ceases. The solvent is evaporated to yield the title compound.

Workup

  1. customThe solvent is evaporated

Sources & evidence

ORD record
ord-8f961c0811564b9cb71dcafe6a28802f
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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