Sodium Hydroxide → HCID 86733322, compound

HRID 1606471Notes

Reaction equation

HRID 1606471 reaction equation
[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C:18]2=[CH:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.BrN1C(=[O:30])CCC1=O.Cl(O)(=O)(=O)=O.[OH-].[Na+]>O1CCOCC1.O.C(O)(=O)C>[O:30]1[C@@H:17]2[C@:18]31[C@H:7]([C@H:8]1[C@:15]([CH3:23])([CH2:16]2)[C@@H:11]([C:12](=[O:14])[CH3:13])[CH2:10][CH2:9]1)[CH2:6][CH2:5][C@@H:4]1[C@:19]3([CH3:22])[CH2:20][CH2:21][C@@H:2]([OH:1])[CH2:3]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 67184N-bromobutanimideHCID 13940962HCID 13940962, compound

Product 1

HCID 86733322HCID 86733322, compoundYield 25.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

3α-Hydroxy-5α-pregn-9(11)-en-20-one (500 mg.) was dissolved in dioxan (50 ml.) and water (12.5 ml.) under nitrogen; N-bromosuccinimide (325 mg.) was added followed by perchloric acid (60% w/v; 0.175 ml.) in water (5 ml.) and the reaction was allowed to stand at room temperature for 5 min. The pH was adjusted to 11.7 with 2N sodium hydroxide and the reaction mixture was allowed to stand at room temperature for a further 15 mins. The pH was adjusted to 6 with glacial acetic acid and the mixture was poured into water. The steroid was extracted with chloroform and triturated with ether to give a white solid; crystallisation from ether followed by crystallisation from methyl acetate-petrol gave the title compound (134 mg.), m.p. 160°-162°, [α]D + 101°.

Workup

  1. waitto stand at room temperature for a further 15 mins
  2. extractionThe steroid was extracted with chloroform
  3. customtriturated with ether
  4. customto give a white solid
  5. customcrystallisation from ether
  6. customfollowed by crystallisation from methyl acetate-petrol

Sources & evidence

ORD record
ord-38e0d0aa45d841d7ac2803013346673c
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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