Реакция #40602

Уравнение реакции

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

Выход 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

Выход 84.0%

Растворители

CH2Cl2 MeOH

Условия реакции

Обработка

1. 1
   ФильтрацияThe mixture was filtered
2. 2
   Концентрированиеthe filtrate was concentrated to dryness under reduced pressure
3. 3
   workup.ADDITION2N NaOH (30 mL) was added to the residue
4. 4
   Экстракцияthe mixture was extracted with CH2Cl2 (2×20 mL)
5. 5
   ПромывкаThe combined CH2Cl2 portion was washed with H2O (30 mL)
6. 6
   Сушкаdried (Na2SO4)
7. 7
   ДругоеRemoval of the solvent under reduced pressure

Методика

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.

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