4-Pregnene-3,20-dione-21-ol benzoate → 4,9(11)-Pregnadiene-3,20-dione-21-ol benzoate

HRID 979423Notes

Reaction equation

HRID 979423 reaction equation
[C:1]([O:9][CH2:10][C:11](=[O:32])[C@@H:12]1[C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[CH2:18][CH2:17]3)[CH2:14][CH2:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1SC2(CC[C@@]3(C)C(CC[C@@H]4C3=CC[C@@]3(C)[C@H]4CC[C@@H]3C(=O)COC(=O)C3C=CC=CC=3)=C2)SC1>C(Cl)(Cl)Cl>[C:1]([O:9][CH2:10][C:11](=[O:32])[C@@H:12]1[C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C:26](=[CH:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[CH2:18][CH2:17]3)[CH2:14][CH2:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 156740314-Pregnene-3,20-dione-21-ol benzoateHCID 1860793121-Benzoyloxy-4,9(11)-pregnadiene-3,20-dione-3-ethylenedithioacetal

Product 1

HCID 186079324,9(11)-Pregnadiene-3,20-dione-21-ol benzoateYield 42%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The process described for the preparation of 4-pregnene-3,20-dione-21-ol benzoate (see the further-conversion of the product described in Example 4) is followed by using 4.97 g (9.7 mmoles) of 21-benzoyloxy-4,9(11)-pregnadiene-3,20-dione-3-ethylenedithioacetal as starting material [prepared as described in the preceding Step (a)], except that the crude product is not subjected to chromatography, but it is recrystallized from ethyl acetate under purifying with activated carbon to give 1.8 g (42% yield) of the aimed product, m.p.: 176°-177° C., [α]D =+175.1° (c=1 in chloroform).

Workup

  1. customprepared
  2. customis recrystallized from ethyl acetate
  3. customunder purifying with activated carbon

Sources & evidence

ORD record
ord-caebfe51dc4d41a595d027ecb52358f6
Source dataset
uspto-grants-1987_05
Patent number
US04668437

Reaction notes

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