1-Benzyl-4-piperidone → (+/-)-4-(1,2,3,5,8,8a-Hexahydroindolizin-7-yl)-2-phenyl-3-(pyridin-4-yl)-1H-pyrrole

HRID 1245019Notes

Reaction equation

HRID 1245019 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=O)[C:24](F)(F)F)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Br[C:30]1[C:31](C2C=CN=CC=2)=C(C2C=CC(F)=CC=2)N([Si](C(C)C)(C(C)C)C(C)C)[CH:34]=1.C1C2N(CCC(=O)C2)CC1.C(N1CCC(=O)CC1)C1C=CC=CC=1>>[CH2:34]1[CH:30]2[N:22]([CH2:21][CH:20]=[C:19]([C:11]3[C:12]([C:13]4[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=4)=[C:8]([C:5]4[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=4)[NH:9][CH:10]=3)[CH2:31]2)[CH2:23][CH2:24]1

Participants

5

Reactant 4

HCID 192201-Benzyl-4-piperidoneHCID 11240524Octahydroindolizin-7-oneHCID 219227844-Bromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrroleHCID 219228412-(4-Fluorophenyl)-3-(pyridin-4-yl)-4-(3-trifluoroacetylaminopropyl)-1H-pyrrole

Product 1

HCID 9906007(+/-)-4-(1,2,3,5,8,8a-Hexahydroindolizin-7-yl)-2-phenyl-3-(pyridin-4-yl)-1H-pyrrole

Procedure

In a similar manner to the procedures described in Examples 9(i) and 9(iii) above, coupling, dehydration and desilylation reactions were carried out using 4-bromo-2-phenyl-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrrole (prepared as described in Preparative Example 2 below), instead of 4-bromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrrole, and (±)-1,2,3,5,6,7,8,8a-octahydroindolizine-7-one, instead of 1-benzylpiperidine-4-one, as starting materials to afford a mixture of the title compound and the (1,2,3,5,6,8a-hexahydroindolizin-7-yl) isomer thereof (which is the compound of Example 100 below). The mixture was separated by chromatography on a silica gel column using a 30:1 by volume mixture of ethyl acetate and isopropylamine as the eluant to give the title compound (yield 14%, Rf value=0.24) as a pale brown powder.

Workup

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Sources & evidence

ORD record
ord-5669d0c9495d4e70bbca77b78c652268
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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