Potassium bis(trimethylsilyl)amide → tert-Butyl 4-(prop-2-en-1-yl)piperidine-1-carboxylate
Reaction equation
[CH3:1][Si](C)(C)[N-][Si](C)(C)C.[K+].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH:25]=O)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.C(OCC)(=O)C>[CH2:24]([CH:21]1[CH2:22][CH2:23][N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH2:19][CH2:20]1)[CH:25]=[CH2:1]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of methyltriphenylphosphonium bromide (5.3 g, 14.8 mmol) in THF (50 mL) was cooled to 0° C. under nitrogen. Potassium hexamethyl disilazide (27.7 mL, 0.5M toluene solution, 13.9 mmol) was added and the mixture was stirred for 30 min. A solution of (1-t-butoxycarbonylpiperidin-4-yl)acetaldehyde from Step A (2.25 g, 9.9 mmol) in THF (10 mL) was added and the mixture was warmed to rt. After 30 min, the reaction was complete by tlc analysis. The mixture was diluted with ethyl acetate (200 mL) and washed with water and brine (100 mL each). The organic phase was dried over sodium sulfate and concentrated to give an oil which was purified by FC (75 g silica, 10/1 hexane/ethyl acetate) to afford the title compound (1.61 g).
Workup
- waitAfter 30 min
- washwashed with water and brine (100 mL each)
- dry with materialThe organic phase was dried over sodium sulfate
- concentrationconcentrated
- customto give an oil which
- customwas purified by FC (75 g silica, 10/1 hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-e217916ba0d24f1885aa625385412ef1
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06593346B2
Reaction notes
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