反応 #2254173

反応方程式

BnCl

2

((2S,3S,4aR,8R,8aR)-2,3-Dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)methanol Hydrochloride

K2CO3

→

title compound

収率 97.9%

((2S,3S,4aR,8R,8aR)-6-Benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)methanol

収率 97.9%

溶媒

DMF

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction was stirred at 40° C. overnight
2. 2
   その他The solvent was evaporated in vacuo
3. 3
   workup.ADDITIONHCl was added
4. 4
   workup.DISSOLUTIONto dissolve the residue
5. 5
   洗浄The solution was washed with Et2O
6. 6
   抽出The solution was extracted with EtOAc (2×)
7. 7
   洗浄the combined extracts were washed with water
8. 8
   乾燥brine and then dried over MgSO4
9. 9
   ろ過The solution was filtered
10. 10
    その他the filtrate evaporated in vacuo

実験手順

To a solution of 2 (14.85 g, 50.0 mmol) in DMF (200 mL) was added K2CO3 (17.25 g, 125 mmol) and the mixture was stirred at 40° C. for about 4 hrs. At this point, BnCl (5.7 mL, 50.0 mmol) was added in one portion and the reaction was stirred at 40° C. overnight. The solvent was evaporated in vacuo and the residue was suspended in water (600 mL) and HCl was added to dissolve the residue. The solution was washed with Et2O and then basified with Na2CO3. The solution was extracted with EtOAc (2×) and the combined extracts were washed with water and then brine and then dried over MgSO4. The solution was filtered and the filtrate evaporated in vacuo to give the title compound (17.2 g, >95%) as a colorless to very pale yellow viscous oil which was used without further purification. 1H NMR (CDCl3) 7.3 (m, 5H), 3.6-3.8 (m, 2H), 3.5 (s, 3H), 3.4 (t, 1H), 3.26 (s, 3H), 3.268 (s, 3H), 2.9 (m, 2H), 2.2 (br s, 1H), 2.05 (m, 1H), 1.85 (t, 1H), 1.28 (s, 3H), 1.26 (s, 3H).

出典