4-Methoxy-beta-nitrostyrene → HCID 131726234, compound

HRID 347310Notes

Reaction equation

HRID 347310 reaction equation
C(O[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])C.[CH3:25][O:26][C:27]1[CH:37]=[CH:36][C:30]([CH:31]=[CH:32][N+:33]([O-])=O)=[CH:29][CH:28]=1>>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C@H:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C@H:12]2[N:9]2[CH2:10][CH2:11][C:6]3([C:4](=[O:5])[NH:33][CH2:32][CH:31]3[C:30]3[CH:36]=[CH:37][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[CH2:7][CH2:8]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 2298434-Methoxy-beta-nitrostyreneHCID 66918204HCID 66918204, compound

Product 1

HCID 131726234HCID 131726234, compoundYield 52%

Procedure

As described for example 1b, cis-rac-1-[2-(4-fluoro-phenyl)-cyclohexyl]-piperidine-4-carboxylic acid ethyl ester (800 mg, 2.4 mmol) (using 4-methoxy-beta-nitrostyrene instead of trans-beta-nitrostyrene) was converted to the title compound (642 mg) 52%) which was obtained as a light yellow foam. MS: m/e=513.4 (M+H).

Sources & evidence

ORD record
ord-27826ee2ce1d4cef80fcbb24f36881ab
Source dataset
uspto-grants-2007_02
Patent number
US07173133B2

Reaction notes

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