Chlorotrimethylsilane → 2-(2-Cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethanamine
Reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.[CH:8]1([C:11]2[C:16](/[CH:17]=[CH:18]/[N+:19]([O-])=O)=[CH:15][CH:14]=[C:13]([C:22]([F:25])([F:24])[F:23])[N:12]=2)[CH2:10][CH2:9]1>C1COCC1>[CH:8]1([C:11]2[C:16]([CH2:17][CH2:18][NH2:19])=[CH:15][CH:14]=[C:13]([C:22]([F:25])([F:23])[F:24])[N:12]=2)[CH2:10][CH2:9]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of lithium borohydride (232 μL, 0.465 mmol) in THF was added chlorotrimethylsilane (118 μL, 0.930 mmol) dropwise. After stirring for 15 minutes, argon was bubbled through the reaction mixture for 2 minutes to eliminate any trimethylsilane in the reaction mixture. (E)-2-cyclopropyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridine (30 mg, 0.116 mmol) was added (in 1 mL of THF). The reaction was heated to reflux for 2 hours, cooled to 0° C. and carefully quenched with methanol (1 mL). The reaction mixture was concentrated, diluted with dichloromethane and 20% aqueous KOH. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated to yield 2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethanamine (26 mg, 0.113 mmol, 97.2% yield).
Workup
- customargon was bubbled through the reaction mixture for 2 minutes
- temperatureThe reaction was heated
- temperatureto reflux for 2 hours
- customcarefully quenched with methanol (1 mL)
- concentrationThe reaction mixture was concentrated
- additiondiluted with dichloromethane and 20% aqueous KOH
- customThe layers were separated
- dry with materialthe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a019586482ca4869a98e2a54617693c8
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785445B2
Reaction notes
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