Aluminium lithium hydride → HCID 73236150, compound
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:7][CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][OH:10])([CH3:6])[C:4]#[N:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>COC(C)(C)C>[NH2:5][CH2:4][C:3]([NH:7][CH:8]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][OH:10])([CH3:6])[C:2]([F:17])([F:18])[F:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
31 g (120.0 mmol) of 3,3,3-trifluoro-2-[(2-hydroxy-1-phenylethyl)amino]-2-methylpropanonitrile from Example 48A were initially charged in tert-butyl methyl ether (3.1 l) and cooled to 0° C., 18.25 g (480.2 mmol) of lithium aluminium hydride were added and the reaction mixture was stirred at RT for 16 h. Subsequently, the mixture was cooled to 0° C., first quenched with 24 ml of water, then admixed with 24 ml of 15% aqueous potassium hydroxide solution and 48 ml of water. The resulting mixture was filtered through silica gel and washed with tert-butyl methyl ether. The organic phase was separated off, dried over sodium sulphate, filtered and concentrated. This gave 29.2 g (83% of theory, purity 89%) of the target compound.
Workup
- temperatureSubsequently, the mixture was cooled to 0° C.
- customfirst quenched with 24 ml of water
- filtrationThe resulting mixture was filtered through silica gel
- washwashed with tert-butyl methyl ether
- customThe organic phase was separated off
- dry with materialdried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0aae8984389447229c2d359e50fd6da2
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422285B2
Reaction notes
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