Hydrochloric Acid → HCID 14135842, compound

HRID 482167Notes

Reaction equation

HRID 482167 reaction equation
CO.[O:3]=[C:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@H:6]([C:7](=[O:31])[CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:5]1.Cl>O1CCCC1>[O:3]=[C:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:6]([C:7](=[O:31])[CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14135841HCID 14135841, compound

Product 1

HCID 14135842HCID 14135842, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 3,6-dioxo-5α sterol was prepared by acid-catalyzed isomerization of the 5β sterol. To methanol (250 ml) was added the 3,6-dioxo-5β sterol 1017 (9.6 g, 24 mmol) and tetrahydrofuran (25 ml) to dissolve the sterol completely. Concentrated hydrochloric acid (12.5 ml) was added, and the reaction was allowed to proceed overnight. The solvent was then removed under vacuum to yield 9.6 g (100% yield) of methyl 3,6-dioxo-5α-cholan-24-oate 1018 (see Organic Preparations and Procedures Int. 19(2-3), 1987, 197-208; authors used base-catalyzed isomerization using sodium methoxide rather than HCl).

Workup

  1. customThe solvent was then removed under vacuum

Sources & evidence

ORD record
ord-45d63ac51da24a33b3ddf9439cd69615
Source dataset
uspto-grants-1998_08
Patent number
US05792635

Reaction notes

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