Borane → 3-Methyl-N2-(4-quinolyl)butane-1,2-diamine
Reaction equation
[CH3:1][CH:2]([CH3:18])[CH:3]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1)[C:4]([NH2:6])=O.B>C1COCC1>[CH3:1][CH:2]([CH3:18])[CH:3]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1)[CH2:4][NH2:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Methyl-2-(4-quinolylamino)butanamide (460 mg, 1.9 mmol) was dissolved in anhydrous THF (30 ml) under argon, the mixture was cooled to 0° C. and a 1M solution of borane in anhydrous THF (8 ml, 8 mmol) was added with stirring. Stirring was continued for 1 hour at 0° C., the cooling bath was removed and the mixture was allowed to warm to room temperature overnight with stirring. The mixture was quenched with 1M NaOH and extracted with ethyl acetate. The organic phase was evaporated to dryness under reduced pressure and the residue was purified by column chromatography (pre-packed silica column, gradient of ethyl acetate/methanol containing 1% ammonia). 220 mg was obtained (0.96 mmol, 51%). MS (APCI) m/z=229.8 [M+H]+.
Workup
- stirringStirring
- customthe cooling bath was removed
- temperatureto warm to room temperature overnight
- stirringwith stirring
- customThe mixture was quenched with 1M NaOH
- extractionextracted with ethyl acetate
- customThe organic phase was evaporated to dryness under reduced pressure
- customthe residue was purified by column chromatography (pre-packed silica column, gradient of ethyl acetate/methanol containing 1% ammonia)
- custom220 mg was obtained (0.96 mmol, 51%)
Sources & evidence
- ORD record
- ord-0d1befbb89b84c088279b5edcb6197f7
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877934B2
Reaction notes
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