Ethyl chloroformate → trans-8-Fluoro-5-(p-fluorophenyl)-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole

HRID 27911Notes

Reaction equation

HRID 27911 reaction equation
Cl.C([N:9]1[CH2:29][CH2:28][C@H:12]2[N:13]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][C:19]=3[C@@H:11]2[CH2:10]1)C1C=CC=CC=1.ClC(OCC)=O>>[F:20][C:17]1[CH:16]=[CH:15][C:14]2[N:13]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[C@@H:12]3[CH2:28][CH2:29][NH:9][CH2:10][C@H:11]3[C:19]=2[CH:18]=1

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 70573462trans-2-benzyl-8-fluoro-5-(p-fluorophenyl)-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole hydrochloride

Product 1

HCID 13014387trans-8-Fluoro-5-(p-fluorophenyl)-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole

Procedure

Alternately, dl-trans-2-benzyl-8-fluoro-5-(p-fluorophenyl)-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole hydrochloride is refluxed in the presence of excess ethyl chloroformate or the corresponding methyl, isopropyl or n-butyl chloroformate esters, then hydrolyzed and worked up by the procedure described above to obtain the title compound.

Sources & evidence

ORD record
ord-233bc4fc7b3540898d55f802dc3a4438
Source dataset
uspto-grants-1980_09
Patent number
US04224329

Reaction notes

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