Réaction #79925

Équation de réaction

Intermediate 23

Ethyl-2-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

di-iso-butyl aluminum hydride

→

title compound

Rendement 87.0%

2-Cyclopropyl-6-hydroxymethyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline

Rendement 87.0%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreIt was then quenched with saturated aqueous ammonium chloride solution
2. 2
   workup.ADDITIONdiluted with dichloromethane
3. 3
   Filtrationfiltered over a bed of celite
4. 4
   AutreThe phases were separated
5. 5
   Extractionthe aqueous phase was extracted with dichloromethane (×1)
6. 6
   ExtractionThe combined organic extract
7. 7
   Séchagewas dried over anhydrous sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated in vacuo

Mode opératoire

A stirred cooled (−78° C.)solution of ethyl-2-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro isoquinoline-6-carboxylate (Intermediate 23, 1 g, 3.66 mmol) in anhydrous dichloromethane (20 mL) under argon was treated with a 1M solution of di-iso-butyl aluminum hydride in dichloromethane (10 mL) and the reaction mixture was warmed to −20° C. over 1 h. It was then quenched with saturated aqueous ammonium chloride solution and diluted with dichloromethane and filtered over a bed of celite. The phases were separated and the aqueous phase was extracted with dichloromethane (×1). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as a viscous oil (0.74 g, 87%).

Source