Pyridinium hydrochloride → (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

HRID 221193Notes

Reaction equation

HRID 221193 reaction equation
[C:1]([O:4][CH2:5][C:6]([C:8]1(O)[C@:24]2([CH3:25])[CH:11]([CH:12]3[C:21](=[CH:22][CH2:23]2)[C@:20]2([CH3:26])[C:15](=[CH:16][C:17](=[O:27])[CH:18]=[CH:19]2)[C@@H:14]([CH3:28])[CH2:13]3)[CH2:10][CH2:9]1)=[O:7])(=[O:3])[CH3:2].[C:30]([O-])([O-])([O:32]CC)[CH3:31].Cl.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1>[C:30]([C@@:1]1([CH3:2])[O:3][C@:8]2([C@:24]3([CH3:25])[CH:11]([CH:12]4[C:21](=[CH:22][CH2:23]3)[C@:20]3([CH3:26])[C:15](=[CH:16][C:17](=[O:27])[CH:18]=[CH:19]3)[C@@H:14]([CH3:28])[CH2:13]4)[CH2:10][CH2:9]2)[C:6](=[O:7])[CH2:5][O:4]1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 21584435Pyridinium hydrochlorideHCID 672842222-((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 acetateHCID 86598186Ethyl ortho-acetate

Product 1

HCID 67286271(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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. distillationEthanol is distilled off the reaction mixture

Sources & evidence

ORD record
ord-34542830f273452c91b5fa7f1bc3d88e
Source dataset
uspto-grants-2012_06
Patent number
US08207151B2

Reaction notes

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