Water → tert-Butyl 4-(2-acrylamidoethyl)piperidine-1-carboxylate
Reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.CCN(CC)CC.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26].O>C(Cl)Cl>[C:24]([NH:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)(=[O:27])[CH:25]=[CH2:26]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirred mixture of tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate (1.0 g, 4.38 mmol) in DCM (20 mL) at 0° C., Et3N (1.33 g, 13.14 mmol) was added and the resulting mixture was stirred at 0° C. for 5 min. To this mixture, a solution of acryloyl chloride (0.39 g, 4.38 mmol) in DCM (5 mL) was added dropwise. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was poured into water (20 mL) and extracted with DCM (30 mL×3). The combined organic layer was washed with brine (15 mL×3), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10-50% ethyl acetate/dichloroethane) to afford the desired product (0.6 g, 50% yield) as a solid.
Workup
- stirringThe resulting mixture was stirred at room temperature for 30 min
- extractionextracted with DCM (30 mL×3)
- washThe combined organic layer was washed with brine (15 mL×3)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash column chromatography on silica gel (10-50% ethyl acetate/dichloroethane)
Sources & evidence
- ORD record
- ord-0885efd7755f448f8a95e1167cd514ab
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227978B2
Reaction notes
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