Ethanol → Palladium

HRID 1199165Notes

Reaction equation

HRID 1199165 reaction equation
C(O[C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][C:13](C)=[C:14]2NC(=O)C)[CH2:6]1)(=O)C.[H][H].[Pd:31].[CH2:32]([OH:34])[CH3:33]>[Pd]>[Pd:31].[CH2:32]([OH:34])[CH2:33][C@@H:14]1[C@:15]2([CH3:16])[C@H:11]([C@H:10]3[C@H:19]([CH2:18][CH2:17]2)[C@:20]2([CH3:23])[CH:7]([CH2:6][CH2:5][CH2:22][CH2:21]2)[CH2:8][CH2:9]3)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 702Ethanol2×HCID 5662530017-Acetamido-16-methyl-5,16-androstadien-3beta-ol acetateHCID 178506449HCID 178506449, compound

Product 2

HCID 23938PalladiumYield 5%HCID 5460188Pregnan-21-ol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using the procedure of Hershberg, et al JACS 73, 5073 (1951), 4 can be prepared. More specifically, selective hydrogenation of 17αethinyl-5-androsten-17β-ol (1) in pyridine with 5% palladium on Calcium Carbonate affords the vinyl carbinol (2) in high yield. Reduction of 2 in ethanol with 5% palladium on carbon gives the ethyl carbinol 3 without reducing the 5, 6-double bond. Alternatively, 3 can be prepared directly from 1 using H2 /Pd/C. Exhaustive Catalytic hydrogenation of 3 in ethanol with 5% Pd on C gives the fully saturated pregnanol, 4

Sources & evidence

ORD record
ord-ee92b7a160284ade8b5c6fdffd5c04fd
Source dataset
uspto-grants-1990_02
Patent number
US04898694

Reaction notes

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