p-Toluenesulfonic acid → 11beta-Dipropylaminoacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one

HRID 1701431Notes

Reaction equation

HRID 1701431 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1CO[C:14]([C@@H:16]2[C@:33]3([CH3:34])[C@H:19]([C@H:20]4[C@H:30]([C@@H:31]([O:35][C:36](=[O:45])[CH2:37][N:38]([CH2:42][CH2:43][CH3:44])[CH2:39][CH2:40][CH3:41])[CH2:32]3)[C@:28]3([CH3:29])[C@H:23]([CH2:24][C@H:25]([OH:46])[CH2:26][CH2:27]3)[CH2:22][CH2:21]4)[CH2:18][CH2:17]2)([CH3:15])[O:13]1.C(=O)(O)[O-].[Na+]>CC(C)=O>[OH:46][C@@H:25]1[CH2:26][CH2:27][C@@:28]2([CH3:29])[C@@H:23]([CH2:22][CH2:21][C@@H:20]3[C@@H:30]2[C@@H:31]([O:35][C:36](=[O:45])[CH2:37][N:38]([CH2:39][CH2:40][CH3:41])[CH2:42][CH2:43][CH3:44])[CH2:32][C@@:33]2([CH3:34])[C@H:19]3[CH2:18][CH2:17][C@@H:16]2[C:14](=[O:13])[CH3:15])[CH2:24]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 7058354320,20-Ethylenedioxy-11beta-dipropylaminoacetoxy-5alpha-pregnan-3alpha-ol

Product 1

HCID 2281032311beta-Dipropylaminoacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Toluene-4-sulphonic acid (120 mg) was added to a solution of 20,20-ethylenedioxy-11β-dipropylaminoacetoxy-5α-pregnan-3α-ol (260 mg) in acetone (20 ml). The mixture was kept at room temperature until reaction was judged complete (TLC), when sodium bicarbonate solution was added and the precipitated material collected by filtration. Crystallization from ether-petroleum ether afforded title compound, m.p. 120°-122°, [α]D +92°.

Workup

  1. customThe mixture was kept at room temperature until reaction
  2. additionwas added
  3. filtrationthe precipitated material collected by filtration
  4. customCrystallization from ether-petroleum ether

Sources & evidence

ORD record
ord-c67082fb4a05434f809a275d840f4ae7
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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