Tert-butyl 4-(2-oxo-2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate → Tert-butyl 4-(2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate
Reaction equation
O=[C:2]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1>C1COCC1>[N:18]1([CH2:2][CH2:3][O:4][CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Tert-butyl 4-(2-oxo-2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate (111) (7.5 g, 22.98 mmol) was dissolved in dry THF (100 mL), to this was added borane-methyl sulfide complex (17.23 mL, 34.46 mmol) and the reaction was stirred at 40° C. for 3 hours then at ambient temperature overnight. The gummy mixture was evaporated and was quenched with 2.0 N sodium carbonate (50 mL), extracted with EtOAc (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford tert-butyl 4-(2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate (7.3 g, 95% yield) as a colourless liquid and used without further purification.
Workup
- additionto this was added borane-methyl sulfide complex (17.23 mL, 34.46 mmol)
- customat ambient temperature
- customovernight
- customThe gummy mixture was evaporated
- customwas quenched with 2.0 N sodium carbonate (50 mL)
- extractionextracted with EtOAc (3×75 mL)
- dry with materialthe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-350f7410cec3415984070351999852d4
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129380B2
Reaction notes
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