Reaction #50277

ord-dedaec85bf7843bc866a0ca2b2d1f275

Reaction equation

CCOCO[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(O)(C#CC(=O)O)CC[C@]32O)C1
17-hydroxy-17-carboxyethynyl-3beta-ethoxymethoxy-14-hydroxy-5beta,14beta-androstane
C
charcoal
→
CCOCO[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(O)(CCC(=O)O)CC[C@]32O)C1
17-hydroxy-17-(2-carboxyethyl)-3beta-ethoxymethoxy-14-hydroxy-5beta,14beta-androstane

Reactants

CCOCO[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(O)(C#CC(=O)O)CC[C@]32O)C1
17-hydroxy-17-carboxyethynyl-3beta-ethoxymethoxy-14-hydroxy-5beta,14beta-androstane
C
charcoal

Reagents

[Pd]
palladium

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

A solution of 17-hydroxy-17-carboxyethynyl-3beta-ethoxymethoxy-14-hydroxy-5beta,14beta-androstane (30 mg), prepared as described in Example 12, in ethanol (5 ml), was hydrogenated at 2.72 atmosphere in a Parr apparatus in the presence of 10% palladium over charcoal.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05426179uspto-grants-1995_06