Reaktion #1244850

Reaktionsgleichung

5-(1,3-benzodioxol-5-yl)-3,3-dimethyl-3,4-dihydro-2H-pyrrole

sodium triacetoxyborohydride

sodium

acetic acid

sodium

→

title compound

Ausbeute 79.0%

2-(1,3-benzodioxol-5-yl)-4,4-dimethylpyrrolidine

Ausbeute 79.0%

Lösungsmittel

acetonitrile

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstir for 3 h
2. 2
   workup.ADDITIONAdd more
3. 3
   workup.DISSOLUTIONAfter 0.5 h dissolve
4. 4
   Sonstigethe reaction
5. 5
   Waschenwash with methanol
6. 6
   Extraktionextract with ammonia in methanol
7. 7
   EinengenConcentrate under reduced pressure the basic solution

Vorschrift

To a solution of 5-(1,3-benzodioxol-5-yl)-3,3-dimethyl-3,4-dihydro-2H-pyrrole (363 mg, 1.673 mmol) in acetonitrile (35 mL) add sodium triacetoxyborohydride (390 mg, 1.84 mmol) and stir at room temperature for two days. Then add more sodium triaxetoxyborohydride (390 mg, 1.84 mmol) and acetic acid and stir for 3 h. Add more add sodium triaxetoxyborohydride (390 mg, 1.84 mmol). After 0.5 h dissolve the reaction by adding methanol and load onto an ion-exchange SCX-2 (25 g), wash with methanol and then extract with ammonia in methanol. Concentrate under reduced pressure the basic solution, to afford 289 mg (79%) of the title compound. MS: 220 [M+H]+; 1H NMR (300 MHz, CDCl3): δ 6.90 (s, 1H), 6.72-6.75 (m, 1H), 6.72-6.75 (m, 1H), 5.91 (s, 2H), 4.20-4.25 (m, 1H), 2.68-2.72 (m, 1H), 2.75-2.79 (m, 1H), 1.72-1.98 (m, 2H), 1.45-1.1.53 (m, 1H), 1.10-1.18 (m, 6H).

Quelle