(S)-2-((1-butyrylpiperidin-3-yl)methoxy)-6-nitrobenzonitrile → (S)-2-amino-6-((1-butyrylpiperidin-3-yl)methoxy)benzonitrile
Reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([CH2:12][O:13][C:14]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[C:15]=2[C:16]#[N:17])[CH2:7]1)(=[O:5])[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.C1COCC1.CCOC(C)=O.[Fe]>[NH2:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH2:12][C@H:8]2[CH2:9][CH2:10][CH2:11][N:6]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH2:7]2)[C:15]=1[C:16]#[N:17]Participants
6
Reactant 1
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 70 °C
Procedure
To a solution of (S)-2-((1-butyrylpiperidin-3-yl)methoxy)-6-nitrobenzonitrile (Example 1c, 9.92 g, 32.92 mmol) in acetic acid (60 mL) and THF (60 mL), was added iron powder (5.5 g, 98.76 mmol) at room temperature. The reaction mixture was heated to 70° C. and stirred for 1 hour then cooled to room temperature, diluted with EtOAc, filtered through Celite. The filtrate was concentrated under reduced pressure and then re-dissolved in EtOAc, washed with NaHCO3, water and brine, dried over MgSO4, filtered and evaporated. The residue was crystallized from DCM/EtOAc, to give the title compound as off white solid (9.92 g, 93% for 2 steps). MS 302 (MH+).
Workup
- temperaturethen cooled to room temperature
- filtrationfiltered through Celite
- concentrationThe filtrate was concentrated under reduced pressure
- dissolutionre-dissolved in EtOAc
- washwashed with NaHCO3, water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customThe residue was crystallized from DCM/EtOAc
Sources & evidence
- ORD record
- ord-9fda70e3e47b4b7f819573ee8dfbf124
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09420814B2
Reaction notes
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