1-Fluoro-4-((1E)-2-nitroethenyl)benzene → cis-Rac-1-[2-(4-fluoro-phenyl)-cyclohexyl]-4-[1-(4-fluoro-phenyl)-2-nitro-ethyl]-piperidine-4-carboxylic acid ethyl ester

HRID 347309Notes

Reaction equation

HRID 347309 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[F:25][C:26]1[CH:36]=[CH:35][C:29](/[CH:30]=[CH:31]/[N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1>>[CH2:1]([O:3][C:4]([C:6]1([CH:30]([C:29]2[CH:35]=[CH:36][C:26]([F:25])=[CH:27][CH:28]=2)[CH2:31][N+:32]([O-:34])=[O:33])[CH2:7][CH2:8][N:9]([C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]2[C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 53816801-Fluoro-4-((1E)-2-nitroethenyl)benzeneHCID 66918204HCID 66918204, compound

Product 1

HCID 66918273cis-Rac-1-[2-(4-fluoro-phenyl)-cyclohexyl]-4-[1-(4-fluoro-phenyl)-2-nitro-ethyl]-piperidine-4-carboxylic acid ethyl esterYield 77%

Procedure

As described for example 1b, cis-rac-1-[2-(4-fluoro-phenyl)-cyclohexyl]-piperidine-4-carboxylic acid ethyl ester (1.0 g, 3 mmol) (using 4-fluoro-trans-beta-nitrostyrene instead of trans-beta-nitrostyrene) was converted to the title compound (1.2 g, 77%) which was obtained as a white solid. MS: m/e=501.4 (M+H).

Sources & evidence

ORD record
ord-4ffb9546d2f34736829c1c7923e273aa
Source dataset
uspto-grants-2007_02
Patent number
US07173133B2

Reaction notes

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