Diisopropylethylamine → 4-[3-(1-t-Butoxycarbonylpiperidin-4-yl)propenoyl]nitrobenzene

HRID 976141Notes

Reaction equation

HRID 976141 reaction equation
[Cl-].[Li+].C(N(C(C)C)CC)(C)C.[CH:12]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=O.[N+:27]([C:30]1[CH:46]=[CH:45][C:33]([C:34]([CH2:36]P(=O)(OCC)OCC)=[O:35])=[CH:32][CH:31]=1)([O-:29])=[O:28]>C(#N)C.O>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][CH:14]([CH:12]=[CH:36][C:34]([C:33]2[CH:32]=[CH:31][C:30]([N+:27]([O-:29])=[O:28])=[CH:46][CH:45]=2)=[O:35])[CH2:15][CH2:16]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 11808775Diethyl [2-(4-nitrophenyl)-2-oxoethyl]phosphonate

Product 1

HCID 569933314-[3-(1-t-Butoxycarbonylpiperidin-4-yl)propenoyl]nitrobenzeneYield 73.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

0.28 g of lithium chloride, 0.85 g of diisopropylethylamine and 2.13 g of 4-formyl-l-t-butoxycarbonylpiperidine were added to 2.0 g of diethyl (4-nitrobenzoylmethyl)phosphonate dissolved in 20 ml of acetonitrile, and the mixture was stirred at room temperature for about 3 days. Then, water was added to the reaction mixture, and the mixture was extracted with toluene. The extract was dried over anhydrous sodium sulfate and condensed. The obtained residue was applied to silica gel column chromatography to obtain 1.76 g of the title compound as pale yellow crystal.

Workup

  1. extractionthe mixture was extracted with toluene
  2. dry with materialThe extract was dried over anhydrous sodium sulfate and condensed

Sources & evidence

ORD record
ord-9f7d2904910a4743b4b55aecdf81432b
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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