Hydrochloric Acid → HCID 53861775, compound

HRID 466509Notes

Reaction equation

HRID 466509 reaction equation
Br[C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:21])[C@:16]1([CH3:17])[C:11]([CH2:12][CH2:13][CH2:14][CH2:15]1)=[CH:10][CH2:9]3.[O:22]=O.[OH-].[Na+].Cl>N1C=CC=CC=1.O>[OH:22][C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:21])[C@:16]1([CH3:17])[C:11]([CH2:12][CH2:13][CH2:14][CH2:15]1)=[CH:10][CH2:9]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 14798Sodium HydroxideHCID 10360578HCID 10360578, compound

Product 1

HCID 53861775HCID 53861775, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 16α-Bromo-5-androsten-17-one (7.92 g, 20 mmoles) in pyridine (300 ml) and water (64 ml) in an oxygen atmosphere was added 36 ml (36 mmoles) of 1N NaOH. After stirring the mixture for 15 minutes at room temperature under O2, it was added to 1 L of ice water containing 330 ml of concentrated HCl. The crystallized precipitate which formed was filtered off, washed with water, and recrystallized from methanol as leaflets (2, 80 g), mp 168°-172°. HPLC of the mother liquor on a silica gel column using isopropyl alcohol n-hexane as eluent furnished an additional 1.4 g of light yellow prisms, mp 170°-174°. The total yield of 16α-ol was 3.94 g (68.4%).

Workup

  1. customThe crystallized precipitate which formed
  2. filtrationwas filtered off
  3. washwashed with water
  4. customrecrystallized from methanol as leaflets (2, 80 g), mp 168°-172°

Sources & evidence

ORD record
ord-c0c1c9668dd348cfb2276e961243848f
Source dataset
uspto-grants-1992_10
Patent number
US05157031

Reaction notes

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