تفاعل #616281

معادلة التفاعل

NaOH

(−)-Ipc2BCl

2-(5-chloro-1H-indol-3-yl)ethanamine

benzaldehyde

→

(2′R,3S)-5-chloro-2′-phenylspiro[indoline-3,3′-pyrrolidine]

المردود 35.0%

المذيبات

DCM

DCM

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture was filtered through Celite
2. 2
   تركيزThe filtrate was concentrated in vacuo
3. 3
   workup.DISSOLUTIONThe crude product was dissolved in DCM (35 mL)
4. 4
   workup.STIRRINGThe resulting solution was stirred at about room temperature for about 3 days
5. 5
   workup.STIRRINGthe mixture was stirred for about 15 min
6. 6
   أخرىThe organic layer was separated
7. 7
   استخلاصThe aqueous layer was extracted with DCM
8. 8
   غسيلThe combined organic layers were washed with brine
9. 9
   أخرىdried
10. 10
    تركيزconcentrated
11. 11
    أخرىThe residue was purified by column chromatography (hexane:EtOAc, 1:1)

الإجراء التجريبي

To a solution of 2-(5-chloro-1H-indol-3-yl)ethanamine (1.67 g, 8.58 mmol) in DCM (43 mL) was added benzaldehyde (0.96 g, 9.0 mmol). The reaction mixture was stirred over molecular sieves 4 Å (4.1 g) overnight. The mixture was filtered through Celite. The filtrate was concentrated in vacuo. The crude product was dissolved in DCM (35 mL). A solution of (−)-Ipc2BCl (12.3 g, 38.2 mmol) in DCM (40 mL) was added to the reaction mixture. The resulting solution was stirred at about room temperature for about 3 days. Aqueous 15% NaOH solution (50 mL) was added and the mixture was stirred for about 15 min. The organic layer was separated. The aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (hexane:EtOAc, 1:1) to give the less polar product (2′R,3S)-5-chloro-2′-phenylspiro[indoline-3,3′-pyrrolidine] (0.73 g, 35%). Further elution with EtOAc gave the other diastereomer (2′S,3S)-5-chloro-2′-phenylspiro[indoline-3,3′-pyrrolidine] (0.50 g, 24%). LCMS (APCI+) m/z 285, 287 [M+H]+; Rt=2.35 min.

المصدر