Reacción #40602

Ecuación de reacción

38

(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(Azido)-2-(3-furanyl)-dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

NH4Cl

→

39

Rendimiento 84.0%

(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(Amino)-2-(3-furanyl)-dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

Rendimiento 84.0%

Disolventes

CH2Cl2 MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture was filtered
2. 2
   Concentraciónthe filtrate was concentrated to dryness under reduced pressure
3. 3
   workup.ADDITION2N NaOH (30 mL) was added to the residue
4. 4
   Extracciónthe mixture was extracted with CH2Cl2 (2×20 mL)
5. 5
   LavadoThe combined CH2Cl2 portion was washed with H2O (30 mL)
6. 6
   Secadodried (Na2SO4)
7. 7
   OtroRemoval of the solvent under reduced pressure

Procedimiento

A mixture of 38 (0.08 g, 0.19 mmol), Zn dust (0.16 g, 2.45 mmol) and NH4Cl (g, mmol) in a mixture of CH2Cl2/MeOH (1:4, 20 mL) was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. 2N NaOH (30 mL) was added to the residue and the mixture was extracted with CH2Cl2 (2×20 mL). The combined CH2Cl2 portion was washed with H2O (30 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure afforded 0.06 g (84%) of 39 as a white solid, mp 237-240° C. (EtOAc/n-hexanes.

Fuente