HCID 67057621, compound → HCID 67057593, compound

HRID 1510207Notes

Reaction equation

HRID 1510207 reaction equation
[CH:1]([O:14][CH2:15][CH2:16][C:17]1[CH2:22][CH2:21][N:20](C(OC)=O)[CH2:19][CH:18]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C>[CH:1]([O:14][CH2:15][CH2:16][C:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH:18]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 67057621HCID 67057621, compound

Product 1

HCID 67057593HCID 67057593, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of methyl 4-(2-(benzhydryloxy)ethyl)-5,6-dihydropyridine-1(2H)-carboxylate (6.5 g, 18.49 mmol) in ethanol (25 ml) was added Claisen's alkali (6.457 g KOH dissolved in 5 ml water and 20 ml methanol). The solution was refluxed overnight, concentrated in vacuo, cooled and diluted with water (40 ml) and extracted with ether (3×30 ml). The combined ethereal extract was dried (Na2SO4) and evaporated to afford viscous liquid. The product was purified by column chromatography over silica gel (ethyl acetate:methanol:triethylamine 20:10:2.5) to obtain compound 5 as yellowish viscous liquid (4.8 g, 88%). 1H-NMR (CDCl3; 400 MHz): 2.03 (brm, 2H, H-3), 2.29-2.32 (t, 2H, J=6.4 Hz, OCH2CH2), 2.92-2.95 (t, 2H, J=5.6 Hz, H-2), 3.31 (brs, 2H, H-6), 3.49-3.53 (t, 2H, OCH2CH2), 5.32 (s, 1H, PhCH(O)Ph), 5.41 (brs, 1H, CH═C), 5.76 (brs, 1H, —NH), 7.17-7.33 (m, 10H, ArH).

Workup

  1. temperatureThe solution was refluxed overnight
  2. concentrationconcentrated in vacuo
  3. temperaturecooled
  4. additiondiluted with water (40 ml)
  5. extractionextracted with ether (3×30 ml)
  6. extractionThe combined ethereal extract
  7. dry with materialwas dried (Na2SO4)
  8. customevaporated
  9. customto afford viscous liquid
  10. customThe product was purified by column chromatography over silica gel (ethyl acetate:methanol:triethylamine 20:10:2.5)

Sources & evidence

ORD record
ord-d9de5ac2314b44868f4f55d89f8ed57c
Source dataset
uspto-grants-2012_07
Patent number
US08211916B2

Reaction notes

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