Hydrogen Bromide → HCID 86733284, compound

HRID 1606342Notes

Reaction equation

HRID 1606342 reaction equation
[OH:1][C@@H:2]1[C@@H:21]([O:22][CH3:23])[CH2:20][C@@:19]2([CH3:24])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:25])[CH2:16][C@@:15]2([CH3:26])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[BrH:27].BrBr.O>CO.C(O)(=O)C>[Br:27][CH2:13][C:12](=[O:14])[C@@H:11]1[C@:15]2([CH3:26])[C@H:8]([C@H:7]3[C@H:18]([C:17](=[O:25])[CH2:16]2)[C@:19]2([CH3:24])[C@H:4]([CH2:3][C@H:2]([OH:1])[C@@H:21]([O:22][CH3:23])[CH2:20]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 24408BromineHCID 86733129HCID 86733129, compound

Product 1

HCID 86733284HCID 86733284, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 3α-hydroxy-2β-methoxy-5α-pregnane-11,20-dione (2g.) in methanol (15 ml.) was treated with hydrobromic acid in glacial acetic acid (3 drops). The mixture was stirred at room temperature and bromine (530 mg.) in methanol (1.45 ml.) was added dropwise over a period of 30 minutes. The mixture was stirred for a further 30 minutes and poured into water, stirred, filtered, washed with water and dried. Purification by preparative tlc, followed by crystallisation from ethyl acetate and petrol gave the title compound (250mg) as colourless plates; m.p. 185°-188° [α]D + 104°.

Workup

  1. stirringThe mixture was stirred for a further 30 minutes
  2. stirringstirred
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. customPurification by preparative tlc
  7. customfollowed by crystallisation from ethyl acetate and petrol

Sources & evidence

ORD record
ord-27e6b68f01004539b4630b7ccafb4a10
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

Loading…