Benzyl Bromide → Ethyl {cis-1-benzyl-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][NH:13][C@@H:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(#N)C>[CH2:30]([N:13]1[CH2:14][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11][C@@H:12]1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of ethyl {cis-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate (2.25 g, 7.86 mmol, step 5 of Example 1), N,N-diisopropylethylamine (1.12 g, 8.64 mmol) in acetonitrile (45 mL) was added benzyl bromide (1.48 g, 8.64 mmol) at room temperature. After stirring at room temperature for 28 h, the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (250 mL). The organic solution was washed with water (100 mL×3), brine (50 mL), dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (4:1) to give 2.44 g (82%) of the title compound as a colorless oil.
Workup
- concentrationthe mixture was concentrated under reduced pressure
- dissolutionThe resulting residue was dissolved in ethyl acetate (250 mL)
- washThe organic solution was washed with water (100 mL×3), brine (50 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (4:1)
Sources & evidence
- ORD record
- ord-de12a02a7d07448bb2c597b2804e663f
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906532B2
Reaction notes
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