Diisobutylaluminumhydride → 2-Cyclopropyl-6-hydroxymethyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline
Reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([CH:16]1[CH2:18][CH2:17]1)[CH2:10][C:9]2([CH3:20])[CH3:19])=O)C.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH:16]1([N:11]2[CH2:10][C:9]([CH3:19])([CH3:20])[C:8]3[C:13](=[CH:14][CH:15]=[C:6]([CH2:4][OH:3])[CH:7]=3)[CH2:12]2)[CH2:18][CH2:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
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%).
Workup
- customIt was then quenched with saturated aqueous ammonium chloride solution
- additiondiluted with dichloromethane
- filtrationfiltered over a bed of celite
- customThe phases were separated
- extractionthe aqueous phase was extracted with dichloromethane (×1)
- extractionThe combined organic extract
- dry with materialwas dried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-6ae2b159f88b455887b5bbdb78468053
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06369225B1
Reaction notes
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