Cesium carbonate → HCID 68661325, compound
Reaction equation
[N:1]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.F[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:16]([O:15][C:13]([N:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][N:10]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[CH2:9][CH2:8]2)[CH2:3][CH2:2]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution of tert-butyl 4,4′-bipiperidine-1-carboxylate (181 mg; 0.674 mmol) in DMF (3 mL) was treated with 4-fluorobenzonitrile (98 mg; 0.809 mmol) and cesium carbonate (264 mg; 0.809 mmol). The mixture was stirred at 70° C. for 18 hr. The mixture was partitioned between isopropyl acetate (25 mL) and pH7 phosphate buffer (10 mL). The organic was washed twice more with pH7 phosphate buffer (2×10 mL). The organic was dried over magnesium sulfate, filtered and evaporated to a solid. The crude product was chromatographed over silica gel (PTLC; 2:1 hex/MTBE). The major band was recovered affording the title compound. LRMS calc: 369.2 obs: 370.1 (M+H), 270.1 (M-BOC+H).
Workup
- customThe mixture was partitioned between isopropyl acetate (25 mL) and pH7 phosphate buffer (10 mL)
- washThe organic was washed twice more with pH7 phosphate buffer (2×10 mL)
- dry with materialThe organic was dried over magnesium sulfate
- filtrationfiltered
- customevaporated to a solid
- customThe crude product was chromatographed over silica gel (PTLC; 2:1 hex/MTBE)
- customThe major band was recovered
Sources & evidence
- ORD record
- ord-f18d89be336042e19e7d424c726b19e0
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445499B2
Reaction notes
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