Hydrogen Bromide → HCID 70586537, compound

HRID 1701433Notes

Reaction equation

HRID 1701433 reaction equation
[CH2:1]([N:5]([CH2:7][C:8]([O:10][C@H:11]1[CH2:30][C@@:29]2([CH3:31])[C@@H:22]([CH2:23][CH2:24][C@@H:25]2[C:26](=[O:28])[CH3:27])[C@H:21]2[C@H:12]1[C@:13]1([CH3:33])[C@@H:18]([CH2:19][CH2:20]2)[CH2:17][C@@H:16]2[O:32][C@@H:15]2[CH2:14]1)=[O:9])[CH3:6])[CH2:2][CH2:3][CH3:4].[BrH:34]>C(Cl)(Cl)Cl>[Br:34][C@H:15]1[CH2:14][C@@:13]2([CH3:33])[C@@H:18]([CH2:19][CH2:20][C@@H:21]3[C@@H:12]2[C@@H:11]([O:10][C:8](=[O:9])[CH2:7][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH3:6])[CH2:30][C@@:29]2([CH3:31])[C@H:22]3[CH2:23][CH2:24][C@@H:25]2[C:26](=[O:28])[CH3:27])[CH2:17][C@@H:16]1[OH:32]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 86736866HCID 86736866, compound

Product 1

HCID 70586537HCID 70586537, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 11β-(N-butyl-N-methylaminoacetoxy)-2α,3α-epoxy-5α-pregnan-20-one (1.6 g) and aqueous 47% hydrobromic acid (2 ml) in chloroform (100 ml) was stirred at room temperature for 1 hour. The solution was washed with dilute sodium bicarbonate solution and water, dried and evaporated in vacuo to give a foam. Crystallization from ethyl acetate-petroleum ether afforded title compound, m.p. 108°-110°, [α]D +95° (1.303 g).

Workup

  1. washThe solution was washed with dilute sodium bicarbonate solution and water
  2. customdried
  3. customevaporated in vacuo
  4. customto give a foam
  5. customCrystallization from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-3896e1fc6b984fbd8e0a5f5ab3d38009
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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