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

HRID 232799

Reaction equation

HRID 232799 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-93d06620dbbe494aa2241caf1670dcef
Source dataset
uspto-grants-1997_01
Patent number
US05591733

Linked notes

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