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

HRID 918415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918415
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionis added
  2. customare removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9c873323b49c432aba26e9e91a416864
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03971773

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