반응 #40602

반응 방정식

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

수율 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

수율 84.0%

용매

CH2Cl2 MeOH

반응 조건

후처리

1. 1
   여과The mixture was filtered
2. 2
   농축the filtrate was concentrated to dryness under reduced pressure
3. 3
   workup.ADDITION2N NaOH (30 mL) was added to the residue
4. 4
   추출the mixture was extracted with CH2Cl2 (2×20 mL)
5. 5
   세척The combined CH2Cl2 portion was washed with H2O (30 mL)
6. 6
   건조dried (Na2SO4)
7. 7
   기타Removal of the solvent under reduced pressure

실험 절차

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.

출처