反応 #40602

反応方程式

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

収率 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

収率 84.0%

溶媒

CH2Cl2 MeOH

反応条件

後処理

1. 1
   ろ過The mixture was filtered
2. 2
   濃縮the filtrate was concentrated to dryness under reduced pressure
3. 3
   workup.ADDITION2N NaOH (30 mL) was added to the residue
4. 4
   抽出the mixture was extracted with CH2Cl2 (2×20 mL)
5. 5
   洗浄The combined CH2Cl2 portion was washed with H2O (30 mL)
6. 6
   乾燥dried (Na2SO4)
7. 7
   その他Removal of the solvent under reduced pressure

実験手順

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.

出典