Hydrochloric Acid → 3alpha-Hydroxy-5alpha-androstane-17beta-carboxylic acid

HRID 232799

Reaktionsgleichung

Reaktionsgleichung von HRID 232799
[OH-:1].[Na+].BrBr.Br[O-].[Na+].[OH:8][C@@H:9]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C:19](=[O:21])C)[CH2:10]1.Cl>O.O1CCOCC1>[OH:8][C@@H:9]1[CH2:10][CH2:11][C@@:26]2([CH3:29])[C@@H:27]([CH2:12][CH2:13][C@@H:14]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C:19]([OH:21])=[O:1])[CH2:28]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 24408BromineHCID 92786AllopregnanoloneHCID 23673712Sodium hypobromite

Produkt 1

HCID 186531443alpha-Hydroxy-5alpha-androstane-17beta-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of sodium hydroxide (1.1 g) in water (18 mL) was stirred at -5° C. and bromine (0.4 mL) was added very slowly. Cold dioxane (12 mL) was added and the resulting sodium hypobromite solution was added to a solution of 3α-hydroxy-5α-pregnane-20-one (0.6 g) in dioxane (30 mL) at 0° C. The resulting mixture was kept at this temperature for 1 hr., neutralized with concentrated hydrochloric acid and poured into water. Excess 2N hydrochloric acid was then added and the precipitated solid was collected by filtration and dried in vacuo which gave the title compound.

Aufarbeitung

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried in vacuo which

Quellen und Nachweise

ORD-Eintrag
ord-93d06620dbbe494aa2241caf1670dcef
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591733

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