反応 #3104

反応方程式

sodium cyanoborohydride

HCl

ethyl 2-(4-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4,5-dihydro-3H -pyrrole-3-carboxylate

→

title compound

収率 96.8%

Ethyl 2-(4-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-pyrrolidine 3-carboxylate

収率 96.8%

溶媒

ethanol

反応条件

後処理

1. 1
   その他Into a 12-L flask equipped with magnetic stirring, addition funnel, temperature probe, and nitrogen inlet
2. 2
   その他The reaction vessel was degassed with nitrogen
3. 3
   workup.ADDITIONAbsolute 3.7 L ethanol and 1.12 L of THF were added
4. 4
   workup.ADDITIONwas then added
5. 5
   workup.ADDITIONafter addition
6. 6
   その他After the starting material was consumed
7. 7
   workup.ADDITION0.5 L of 7% aq. NaHCO3 was added
8. 8
   濃縮The reaction mixture was concentrated
9. 9
   workup.ADDITIONdiluted with 5 L ethyl acetate
10. 10
    洗浄The organic layer was washed twice with 2 L of 7% aq. NaHCO3 and once with 2.5 L of 23% aq. NaCl
11. 11
    乾燥the dried over 190 g MgSO4
12. 12
    ろ過filtered
13. 13
    濃縮concentrated

実験手順

Into a 12-L flask equipped with magnetic stirring, addition funnel, temperature probe, and nitrogen inlet was charged 0.460 kg ethyl 2-(4-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4,5-dihydro-3H -pyrrole-3-carboxylate (1.25 mol). The reaction vessel was degassed with nitrogen. Absolute 3.7 L ethanol and 1.12 L of THF were added. 31 mg bromocresol green and 94.26 g sodium cyanoborohydride (1.5 mol) were added. A solution containing 400 mL absolute ethanol and 200 mL of 12M HCl was then added. The reaction mixture was stirred for 30 minutes after addition was complete. After the starting material was consumed, 0.5 L of 7% aq. NaHCO3 was added. The reaction mixture was concentrated and diluted with 5 L ethyl acetate. The organic layer was washed twice with 2 L of 7% aq. NaHCO3 and once with 2.5 L of 23% aq. NaCl, the dried over 190 g MgSO4, filtered, and concentrated to give 447 g of the title compound as a thick yellow oil.

出典