Spironolactone → 10,13-Dimethyl-1,8,9,10,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2'-oxolane]-3,5'(2H)-dione

HRID 2285438Notes

Reaction equation

CC(S[C@H:5]1[C@H:15]2[C@H:16]3[C@:20]([CH3:23])([CH2:21][CH2:22][C@@H:14]2[C@:13]2([CH3:29])[C:7](=[CH:8][C:9]([CH2:11][CH2:12]2)=[O:10])[CH2:6]1)[C@@:19]1([O:28][C:26](=[O:27])[CH2:25][CH2:24]1)[CH2:18][CH2:17]3)=O.[OH-].[Na+].C[O-].[Na+]>>[CH3:29][C:13]12[CH:14]3[CH2:22][CH2:21][C:20]4([CH3:23])[C:19]5([O:28][C:26](=[O:27])[CH2:25][CH2:24]5)[CH2:18][CH2:17][CH:16]4[CH:15]3[CH:5]=[CH:6][C:7]1=[CH:8][C:9](=[O:10])[CH2:11][CH2:12]2

Participants

Reactant 3

HCID 5833Spironolactone

HCID 14798Sodium Hydroxide

HCID 10942334Sodium Methoxide

Product 1

HCID 31926010,13-Dimethyl-1,8,9,10,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2'-oxolane]-3,5'(2H)-dione

Procedure

The 7β-acetylthio derivative can be converted into the spironolactone by treating the 7β-acetylthio derivative with a base such as sodium hydroxide or sodium methoxide to give the starting material, 17-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid γ-lactone, followed by the addition reaction with thioacetic acid. (This method is hereinafter referred to as "elimination-addition method".)

Sources & evidence

ORD record: ord-2b7a4c30345a404bad40370f55516315
Source dataset: uspto-grants-1982_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04323500

Reaction notes

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