Reaction #1583902

ord-53cb4cc4f8e44a77bff0acc53b44c73f

Reaction equation

CC(=O)OCC(=O)C1(O)CCC2C3C[C@H](C)C4=CC(=O)C=C[C@]4(C)C3=CC[C@@]21C
2-((6S,10R,13S)-17-hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
CCOC(C)([O-])[O-]
ethyl orthoacetate
Cl.c1cc[nH+]cc1
pyridinium hydrochloride
→
CC(=O)[C@]1(C)OCC(=O)[C@]2(CCC3C4C[C@H](C)C5=CC(=O)C=C[C@]5(C)C4=CC[C@@]32C)O1
(2′R,4′R,6S,10R,13S)-2′-acetyl-2′,6,10,13-tetramethyl-7,8,10,12,13,14,15,16-octahydrospiro[cyclopenta[a]phenanthrene-17,4′-[1,3]dioxane]-3,5′(6H)-dione

Reactants

CC(=O)OCC(=O)C1(O)CCC2C3C[C@H](C)C4=CC(=O)C=C[C@]4(C)C3=CC[C@@]21C
2-((6S,10R,13S)-17-hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
CCOC(C)([O-])[O-]
ethyl orthoacetate
Cl.c1cc[nH+]cc1
pyridinium hydrochloride

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.DISTILLATIONEthanol is distilled off the reaction mixture

Procedure

2-((6S,10R,13S)-17-hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate is dissolved in toluene and heated with 1.5 equivalents of ethyl orthoacetate and a trace of pyridinium hydrochloride. Ethanol is distilled off the reaction mixture to drive it to completion.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09198921B2uspto-grants-2015_12