Tetrahydrofuran → tert-Butyl 3-[3-(1-aminoethyl)-5-chloro-2-methoxy-6-methylphenyl]azetidine-1-carboxylate
Reaction equation
[C:1]([C:4]1[C:5]([O:23][CH3:24])=[C:6]([CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:31].[Na+].C1COCC1>CO.C(#N)C>[NH2:31][CH:1]([C:4]1[C:5]([O:23][CH3:24])=[C:6]([CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A mixture of tert-butyl 3-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)azetidine-1-carboxylate (0.56 g, 1.6 mmol), ammonium acetate (1.0 g, 20 mmol) and 1.0 M sodium cyanoborohydride in THF (4.0 mL, 4.0 mmol) in methanol (4 mL)/acetonitrile (4 mL) was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution, extracted with dichloromethane. The organic extracts were dried over MgSO4 and concentrated to give the crude product, which was used in the next step without further purifications. LCMS calculated for C18H27ClN2O3Na (M+Na)+: m/z=377.2. found: 377.1.
Workup
- temperatureThe mixture was cooled to room temperature
- customquenched with sat. NaHCO3 solution
- extractionextracted with dichloromethane
- dry with materialThe organic extracts were dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c0f693bc69194aeb86d58fb5cb3ea9a7
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096600B2
Reaction notes
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