Hydrogen Bromide → HCID 86733284, compound

HRID 1077018Notes

Reaction equation

HRID 1077018 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 (2 g.) 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 t.l.c., followed by crystallisation from ethyl acetate and petrol gave title compound (250 mg.) 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 t.l.c
  7. custom, followed by crystallisation from ethyl acetate and petrol

Sources & evidence

ORD record
ord-fd4ebfe1832246469867a81458be8e0c
Source dataset
uspto-grants-1976_05
Patent number
US03959260

Reaction notes

Loading…