1,8-Diazabicyclo(5.4.0)undec-7-ene → Benzyl 4-(2-methoxy-2-oxoethyl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 1442908Notes

Reaction equation

HRID 1442908 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]=[C:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.N12CCCN=C1CCCCC2>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH:6]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57362584Benzyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate

Product 1

HCID 59555173Benzyl 4-(2-methoxy-2-oxoethyl)-3,6-dihydropyridine-1(2H)-carboxylateYield 0%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of benzyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate (5.25 g, 18.1 mol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.71 mL, 18.1 mol) in DMF (120 mL) was stirred at room temperature. After 3 d the reaction was diluted with water and extracted with ether (4×). The organic washes were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of 5 to 30% ethyl acetate:hexanes to give the title compound (2.44 g). MS: m/z=290.1 (M+1). 1H NMR (500 MHz, CDCl3) δ 7.30-7.25 (m, 5H), 5.5 (brs, 1H), 5.2 (s, 2H), 4.0 (brs, 2H), 3.7 (s, 3H), 3.6 (brs, 2H), 3.0 (s, 2H), 2.2 (brs, 2H).

Workup

  1. extractionextracted with ether (4×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of 5 to 30% ethyl acetate

Sources & evidence

ORD record
ord-55020ccb0bd8413ba7176b2deb000342
Source dataset
uspto-grants-2010_02
Patent number
US07659264B2

Reaction notes

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