2-(2-Diazoethoxy)oxane → 21-Chloro-11beta,17-dihydroxy-16alpha-[2-(tetrahydropyran-2-yloxy)ethoxy]-pregna-1,4-diene-3,20-dione

HRID 918415Notes

Reaction equation

HRID 918415 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]=[N+]=[N-].[Cl:12][CH2:13][C:14](=[O:38])[C@:15]1([OH:37])[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@H:29]([C@@H:30]([OH:34])[CH2:31]2)[C@:27]2([CH3:28])[C:22](=[CH:23][C:24](=[O:35])[CH:25]=[CH:26]2)[CH2:21][CH2:20]3)[CH2:17][C@H:16]1[OH:36]>CCOCC.CO>[Cl:12][CH2:13][C:14](=[O:38])[C@:15]1([OH:37])[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@H:29]([C@@H:30]([OH:34])[CH2:31]2)[C@:27]2([CH3:28])[C:22](=[CH:23][C:24](=[O:35])[CH:25]=[CH:26]2)[CH2:21][CH2:20]3)[CH2:17][C@H:16]1[O:36][CH2:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1

Participants

5

Reactant 2

HCID 215208792-(2-Diazoethoxy)oxaneHCID 8673375321-Chloro-11beta,16alpha,17-trihydroxypregna-1,4-diene-3,20-dione

Product 1

HCID 2279178221-Chloro-11beta,17-dihydroxy-16alpha-[2-(tetrahydropyran-2-yloxy)ethoxy]-pregna-1,4-diene-3,20-dione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-(tetrahydropyran-2-yloxy)-1-diazoethane (prepared from 0.21 mole of N-[2-(tetrahydropyran-2-yloxy)ethyl]urea as described in Example 1) in 400 ml of 3:1 ether-pentane is diluted with 100 ml each of ether and methanol at 0°C and stirred vigorously while 21-chloro-11β,16α,17-trihydroxypregna-1,4-diene-3,20-dione, 16,17-cycloborate (12 mmoles) is added. After nitrogen evolution ceases the solvents are removed in vacuo to yield the title compound.

Workup

  1. additionis added
  2. customare removed in vacuo

Sources & evidence

ORD record
ord-9c873323b49c432aba26e9e91a416864
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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