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

HRID 1664798Notes

Reaction equation

HRID 1664798 reaction equation
N1CCCN2CCCCCC=12.[CH3:12][O:13][C:14](=[O:32])[CH:15]=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:18][CH2:17]1>CN(C)C=O.O>[CH3:12][O:13][C:14](=[O:32])[CH2:15][C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:18][CH:17]=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 46.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine (2.71 mL, 18.2 mmol) was added to a solution of benzyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate (5.25 g, 18.2 mmol) in N,N-dimethylformamide (120 mL). After 3 days, the reaction mixture was diluted with water and extracted with ether (4×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane→85% dichloromethane/ethyl acetate)] gave the title compound (2.43 g). MS 290.1 (M+1).

Workup

  1. extractionextracted with ether (4×)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography [100% dichloromethane

Sources & evidence

ORD record
ord-7ed1e1fde32748018edc731c0e3b34cb
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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