| Identification | Back Directory | [Name]
Methyl 1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylate | [CAS]
88928-69-2 | [Synonyms]
methyl 1-benzyl-3,6-dihydro-2H-pyridine-5-carboxylate
Methyl 1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylate | [Molecular Formula]
C14H17NO2 | [MDL Number]
MFCD26387489 | [MOL File]
88928-69-2.mol | [Molecular Weight]
231.29 |
| Questions And Answer | Back Directory | [Synthesis]
To a solution of β-ketoester 132 (12.6 g, 0.05 mol) in MeOH, NaBH4
(0.97 g, 0.03 mol) was added in portions at 0 ºC. The reaction mixture
was stirred at room temperature for 2 hours. MeOH was removed on
rotavapor, water was added to it and extracted with EtOAc. The
organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and
concentrated under reduced pressure to furnish a faint yellow syrup. To the solution of this
syrup in DCM, Et3N (10.65 ml, 0.08 mol) was added and cooled to 0 ºC, MsCl (4.35 ml,
0.05 mol) was added drop-wise via syringe at 0 ºC. The reaction mixture was allowed to
warm gradually and left overnight. It was observed that the mesylate was formed smoothly
and subsequently underwent elimination under reaction conditions to afford the desired
olefin. The reaction mixture was washed with water, brine and dried over anhydrous
Na2SO4. The organic phase was filtered and concentrated under reduced pressure and the
resultant residue was chromatographed over silica gel to furnish olefin 127 as a pale yellow
syrup (8.84 g).
 |
|
|