2-(1-Diazoethyl)-2-phenyl-1,3-dioxolane → 21-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-[(3-oxo-3-phenylprop-2-yl)oxy]pregna-1,4-diene-3,20-dione

HRID 918387Notes

Reaction equation

[C:1]1([C:7]2([C:12](=[N+]=[N-])[CH3:13])[O:11]CCO2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:16][CH2:17][C:18](=[O:43])[C@:19]1([OH:42])[C@:36]2([CH3:37])[C@H:22]([C@H:23]3[C@:33]([F:39])([C@@H:34]([OH:38])[CH2:35]2)[C@:31]2([CH3:32])[C:26](=[CH:27][C:28](=[O:40])[CH:29]=[CH:30]2)[CH2:25][CH2:24]3)[CH2:21][C@H:20]1[OH:41]>CO>[Cl:16][CH2:17][C:18](=[O:43])[C@:19]1([OH:42])[C@:36]2([CH3:37])[C@H:22]([C@H:23]3[C@:33]([F:39])([C@@H:34]([OH:38])[CH2:35]2)[C@:31]2([CH3:32])[C:26](=[CH:27][C:28](=[O:40])[CH:29]=[CH:30]2)[CH2:25][CH2:24]3)[CH2:21][C@H:20]1[O:41][CH:12]([C:7](=[O:11])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-phenyl-2-(1-diazoethyl)dioxolane in 3:2 ether-pentane is diluted with methanol and cooled to 0°C. 21-Chloro-9-fluoro-11β,16α,17-trihydroxypregna-1,4-diene-3,20-dione, 16,17-cycloborate is added in portions until nitrogen evolution ceases. The solvent is removed in vacuo.

Workup

customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-fe32e0c37f804cbfa7576eb9cca542e4
Source dataset: uspto-grants-1976_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03971772

Reaction notes

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