(3-Diazoprop-1-en-2-yl)benzene → 21-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-[(2-phenyl-2-propenyl)oxy]-pregna-1,4-diene-3,20-dione

HRID 918380Notes

Reaction equation

HRID 918380 reaction equation
[C:1]1([C:7]([CH:9]=[N+]=[N-])=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][CH2:13][C:14](=[O:39])[C@:15]1([OH:38])[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@:29]([F:35])([C@@H:30]([OH:34])[CH2:31]2)[C@:27]2([CH3:28])[C:22](=[CH:23][C:24](=[O:36])[CH:25]=[CH:26]2)[CH2:21][CH2:20]3)[CH2:17][C@H:16]1[OH:37]>CCOCC.CCCCC.CO>[Cl:12][CH2:13][C:14](=[O:39])[C@:15]1([OH:38])[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@:29]([F:35])([C@@H:30]([OH:34])[CH2:31]2)[C@:27]2([CH3:28])[C:22](=[CH:23][C:24](=[O:36])[CH:25]=[CH:26]2)[CH2:21][CH2:20]3)[CH2:17][C@H:16]1[O:37][CH2:9][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH2:8]

Participants

6

Reactant 2

HCID 21520875(3-Diazoprop-1-en-2-yl)benzeneHCID 8673374021-Chloro-9-fluoro-11beta,16alpha,17-trihydroxypregna-1,4-diene-3,20-dione

Product 1

HCID 8673374521-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-[(2-phenyl-2-propenyl)oxy]-pregna-1,4-diene-3,20-dioneYield 47.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

A solution of 2-phenyl-3-diazo-1-propene (prepared from 28.5 g of N-(2-phenyl-2-propenyl)ethyl carbamate, prepared as described in Example 4) in 700 ml of ether and 50 ml of pentane is diluted with 150 ml of methanol at 0°C and 10 g of 21-chloro-9-fluoro-11β,16α,17-trihydroxypregna-1,4-diene-3,20-dione, 16,17-cycloborate is added in portions. After nitrogen evolution ceases the solvents are removed in vacuo and the residue is recrystallized from methanol to give 6.1 g of 21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-phenyl-2-propenyl)oxy]-pregna-1,4-diene-3,20-dione, melting point 212°-214°C.

Workup

  1. customare removed in vacuo
  2. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-cf509e8590d14a0cb1303a7392a58312
Source dataset
uspto-grants-1976_07
Patent number
US03971772

Reaction notes

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