Trifluoroacetic acid → HCID 86736845, compound

HRID 1449247Notes

Reaction equation

HRID 1449247 reaction equation
FC(F)(F)C(O)=O.C1C=CC=CC=1.CCCCCC.[O:20]=[C:21]1[CH:30]2[C:25]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[CH:40]=3)([CH2:26][C:27](=[O:38])[CH:28](C(OC(C)(C)C)=O)[CH2:29]2)[CH2:24][CH2:23][N:22]1[CH3:47]>CO.C1C=CC=CC=1>[O:20]=[C:21]1[C@H:30]2[C@@:25]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[CH:40]=3)([CH2:26][C:27](=[O:38])[CH2:28][CH2:29]2)[CH2:24][CH2:23][N:22]1[CH3:47]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 110624Benzene hexaneHCID 12947557HCID 12947557, compound

Product 1

HCID 86736845HCID 86736845, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

In a process of preparing 4a-aryldecahydroisoquinolines the steps consisting essentially of the conversion of nipecotates to substituted methylenepiperidone and carboxylic ring formation according to the following reaction system: ##STR10## wherein 4-carboxymethyl-4-(3'-methoxyphenyl)-1-methyl-3-methylene-2-piperidone (29) is converted to an imidazolide (31) by the action of carbonyldiimidazole in CHCl3 /THF and subsequently with the magnesium enolate of tert-butyl hydrogen malonate to produce tert-butyl 4-[4'-[4'-(3"-methoxy-phenyl)-1'-methyl-3'-methylene-2'-oxopiperidyl]]-3-oxobutyrate (32) and this material 32 is cyclized by an alkali metal methanolate dissolved in methanol to tert-butyl 1,6-dioxo-4a-(3'-methoxyphenyl)-2-methyl-decahydroisoquinoline-7-carboxylate (33) and subsequently 33 is treated with trifluoroacetic acid in benzene and subsequent recovery by recrystallization from a benzene-hexane mixture to produce trans 1,6-dioxo-4a-(3'-methoxyphenyl)-2-methyl-decahydroisoquinoline (9).

Sources & evidence

ORD record
ord-9c08f7a5a76a4017a96ddb7bab9cee20
Source dataset
uspto-grants-1980_02
Patent number
US04189583

Reaction notes

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