تفاعل #40602

معادلة التفاعل

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

المردود 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

المردود 84.0%

المذيبات

CH2Cl2 MeOH

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture was filtered
2. 2
   تركيزthe filtrate was concentrated to dryness under reduced pressure
3. 3
   workup.ADDITION2N NaOH (30 mL) was added to the residue
4. 4
   استخلاصthe mixture was extracted with CH2Cl2 (2×20 mL)
5. 5
   غسيلThe combined CH2Cl2 portion was washed with H2O (30 mL)
6. 6
   تجفيفdried (Na2SO4)
7. 7
   أخرىRemoval of the solvent under reduced pressure

الإجراء التجريبي

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.

المصدر