반응 #92108

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Intermediate 24E

Methyl 5-bromo-3,3-dimethyl-3,4-dihydroisoquinoline-2 (1H)-carboxylate

KOH

→

Intermediate 24

수율 40.5%

5-Bromo-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

수율 40.5%

용매

H2O

ethylene glycol

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled
2. 2
   추출extracted with EtOAc twice
3. 3
   추출The combined organics were extracted with 1.5 N HCl solution
4. 4
   추출extracted with EtOAc twice
5. 5
   세척the combined organics were washed with H2O, brine
6. 6
   건조dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

To a solution of Intermediate 24E (4.6 g) in ethylene glycol (50 mL) was added 50% aqueous KOH solution (23 mL) and the reaction was heated at 150° C. for 3 days. The reaction mixture was cooled, diluted with H2O, extracted with EtOAc twice. The combined organics were extracted with 1.5 N HCl solution, the aqueous layer was basified with 10% NaOH solution, extracted with EtOAc twice and the combined organics were washed with H2O, brine, dried over Na2SO4, filtered and concentrated to give Intermediate 24 (1.5 g, 39.4%) as a brown liquid. MS (ESI) m/z: 242.2 (M+H)+.

출처