Reacción #438657

Ecuación de reacción

methyl amine

compound

1,3-Dibenzyl-4-Formyl-Piperidine-3-Carboxylic Acid Methyl Ester

acetic acid

NaB(OAc)3H

→

3a,5-Dibenzyl-2-Methyl-Octahydro-Pyrrolo[3,4-c]Pyridin-3-One

Disolventes

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe tube was sealed
2. 2
   OtroThe reaction mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate solution
3. 3
   OtroThe organic layer was removed
4. 4
   Lavadothe aqueous layer was washed twice with CH2Cl2
5. 5
   Lavadothe combined organic layers were washed with a saturated aqueous brine solution
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under vacuum
9. 9
   OtroPurification by silica gel chromatography
10. 10
    Otroafforded the less polar isomer of Example 200, Step D (0.034 g) as well as the more polar isomer (0.046 g)

Procedimiento

To a solution of the compound of Example 200, Step C (0.210 g, 0.60 mmol) in dichloroethane (5 mL) in a resealable tube was added acetic acid (0.188 mL, 3.28 mmol), methyl amine (2.0 M in MeOH, 1.64 mL, 3.28 mmol) and NaB(OAc)3H (0.951 g, 4.48 mmol), the tube was sealed and the reaction mixture was heated to 70° C. for 30 h. The reaction mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate solution. The organic layer was removed and the aqueous layer was washed twice with CH2Cl2, the combined organic layers were washed with a saturated aqueous brine solution, dried over Na2SO4, filtered and concentrated under vacuum. Purification by silica gel chromatography employing 5-20% EtOAc/CH2Cl2 as the eluant afforded the less polar isomer of Example 200, Step D (0.034 g) as well as the more polar isomer (0.046 g). Example 200, Step D less polar isomer. +APcl MS (M+1)+ 355; 1H NMR (400 MHz, CDCl3) δ: 7.03-7.37 (arom, series of m, 10 H), 3.54 (m, 2H), 3.24 (m, 1H), 2.70 (s, 3H). More polar isomer: +APcl MS (M+1)+ 355; 1H NMR (400 MHz, CDCl3) δ: 7.15-7.33 (arom, series of m, 10 H), 3.59 (d, 1H), 3.43 (d, 1H), 2.74 (s, 3H).

Fuente