반응 #3104

반응 방정식

sodium cyanoborohydride

HCl

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

→

title compound

수율 96.8%

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

수율 96.8%

용매

ethanol

반응 조건

후처리

1. 1
   기타Into a 12-L flask equipped with magnetic stirring, addition funnel, temperature probe, and nitrogen inlet
2. 2
   기타The 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
   기타After the starting material was consumed
7. 7
   workup.ADDITION0.5 L of 7% aq. NaHCO3 was added
8. 8
   농축The reaction mixture was concentrated
9. 9
   workup.ADDITIONdiluted with 5 L ethyl acetate
10. 10
    세척The organic layer was washed twice with 2 L of 7% aq. NaHCO3 and once with 2.5 L of 23% aq. NaCl
11. 11
    건조the dried over 190 g MgSO4
12. 12
    여과filtered
13. 13
    농축concentrated

실험 절차

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.

출처