p-Toluenesulfonic acid → 3beta,7alpha-Dihydroxy-5-pregnen-20-one

HRID 1681813Notes

Reaction equation

HRID 1681813 reaction equation
[CH3:1][C:2](=[O:22])[C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C@H:10]([CH2:11]CC[CH2:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1.C(O[C:27](=[O:29])[CH3:28])(=O)C.C1(C)C=CC(S(O)(=O)=[O:37])=CC=1>C(O)(=O)C>[OH:29][C@H:27]1[CH2:28][CH2:16][C@@:15]2([CH3:14])[C:10](=[CH:9][C@@H:8]([OH:37])[C@@H:7]3[C@@H:17]2[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:6]3[CH2:5][CH2:4][C@@H:3]2[C:2](=[O:22])[CH3:1])[CH2:11]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 118088365alpha-Pregnan-20-one

Product 1

HCID 99674183beta,7alpha-Dihydroxy-5-pregnen-20-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Reaction of 5α-pregnan-20-one (3) with a mixture of acetic anhydride, acetic acid, and p-toluene sulfonic acid followed by HPLC of the crude product affords the isomeric enol acetates 4 and 5. Epoxidation of 4 and 5 in benzene with m-chloro perbenzoic acid overnight at room temperature furnishes the epoxy acetates 6 and 7. Saponification of both 6 and 7 with methanolic sodium hydroxide gives 17α-hydroxy-5α-pregnan-20-one (8) as a common product.

Sources & evidence

ORD record
ord-f4d2998ee58342abb07d599abee11d7f
Source dataset
uspto-grants-1992_12
Patent number
US05175154

Reaction notes

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