Borane → HCID 66718413, compound
Reaction equation
[O:1]1[CH2:5][CH2:4][C@H:3]([O:6][CH2:7][C:8]2[N:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][CH:9]=2)[CH2:2]1.B>>[O:1]1[CH2:5][CH2:4][C@H:3]([O:6][CH2:7][C:8]2[N:13]=[C:12]([CH2:14][NH2:15])[CH:11]=[CH:10][CH:9]=2)[CH2:2]1Participants
Procedure
(S)-6-(Tetrahydrofuran-3-yloxymethyl)pyridine-2-carbonitrile (0.206 mol, 1 eq) was added to borane (1-M in THF, 290 mL, 0.290 mol, 3 eq) at 0° C. under nitrogen. The reaction was then heated to reflux for 5 hours, cooled to room temperature and quenched with 100 mL methanol (exothermic) and evaporated. 2 M aqueous HCl (310 mL) was added (pH 1) to the combined residues. After the quench, the mixture was brought to pH 7 with 5 M NaOH (35 mL). The aqueous mixture was extracted with 2×500 mL dichloromethane. These organic extracts were discarded. The aqueous phase was brought to pH 14 with 5-N NaOH (100 mL) and extracted with 2×1000 mL DCM. The combined organic extracts (from alkaline solution) were washed with 100 mL saturated brine, dried over Na2SO4 and evaporated to give the title compound (50.70 g, 39% over 2 steps) as an amber oil; LC-MS Retention time 0.62 min; (M+H)+ 205.
Workup
- temperatureThe reaction was then heated
- temperatureto reflux for 5 hours
- customquenched with 100 mL methanol (exothermic)
- customevaporated
- addition2 M aqueous HCl (310 mL) was added (pH 1) to the combined residues
- extractionThe aqueous mixture was extracted with 2×500 mL dichloromethane
- extractionextracted with 2×1000 mL DCM
- washThe combined organic extracts (from alkaline solution) were washed with 100 mL saturated brine
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-2b045066de0941a0a8051d0a95930310
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987279B2
Reaction notes
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