Diethyl Ether → 16alpha-[2-(Tetrahydropyran-2-yloxy)ethoxy]-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

HRID 918384Notes

Reaction equation

HRID 918384 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]=[N+]=[N-].O1CCCCC1OCCNC(N)=O.CCOCC.[OH:30][C@H:31]1[CH2:51][C@@:50]2([CH3:52])[C@@H:42]([CH2:43][C@@H:44]([OH:54])[C@:45]2([OH:53])[C:46](=[O:49])[CH2:47][OH:48])[C@H:41]2[C@H:32]1[C@:33]1([CH3:56])[C:38]([CH2:39][CH2:40]2)=[CH:37][C:36](=[O:55])[CH:35]=[CH:34]1>CO>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][O:54][C@@H:44]1[CH2:43][C@@H:42]2[C@:50]([CH3:52])([CH2:51][C@H:31]([OH:30])[C@H:32]3[C@H:41]2[CH2:40][CH2:39][C:38]2[C@:33]3([CH3:56])[CH:34]=[CH:35][C:36](=[O:55])[CH:37]=2)[C@@:45]1([OH:53])[C:46](=[O:49])[CH2:47][OH:48]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 1104705616alpha-HydroxyprednisoloneHCID 12850116N-{2-[(Oxan-2-yl)oxy]ethyl}ureaHCID 215208792-(2-Diazoethoxy)oxane

Product 1

HCID 2279177516alpha-[2-(Tetrahydropyran-2-yloxy)ethoxy]-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(tetrahydropyran-2-yl)oxy-1-diazoethane (prepared from 69.1 g of N-[2-(tetrahydropyran-2-yl-oxy)ethyl]urea by the procedure described in Example 18) in 600 ml of 3:1 ether-pentane is stirred with 200 ml each of ether and methanol at 0°C. 14 g of 11β,16α,17,21-tetrahydroxypregna-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 dissolved in chloroform and chromatographed on a 150 g-silica gel column. Elution with chloroform and then 1:1 chloroform-ethyl acetate gives 4.0 g of TLC pure 16α-[2-(tetrahydropyran-2-yloxy)ethoxy]11β,17,21-trihydroxypregna-1,4-diene-3,20-dione.

Workup

  1. customare removed in vacuo
  2. dissolutionthe residue is dissolved in chloroform
  3. customchromatographed on a 150 g-silica gel column
  4. washElution with chloroform

Sources & evidence

ORD record
ord-8fa92d9b1e34452e977e54556b950935
Source dataset
uspto-grants-1976_07
Patent number
US03971772

Reaction notes

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