Ethyl Acetate → Tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-hydroxypiperidine-1-carboxylate
Reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([CH2:2][C:1]([O:4][CH2:5][CH3:6])=[O:3])([OH:30])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]Participants
5
Conditions
- Temperature
- -78 °C
Procedure
Ethyl acetate (1.95 ml, 20 mmol) was added dropwise at −78° C. to 1M solution of LiHMDS in THF (20 ml, 20 mmol). After stirring for 10 min at −78° C., 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (3.98 g, 20 mmol) in 8 ml of THF was added dropwise at −78° C. and the dry ice/acetone bath was removed to allow the temperature to slowly reach 0° C. At this temperature, the reaction mixture was quenched by addition of 25 ml of H2O and the mixture was extracted twice with Et2O, the organic layers were washed with brine, dried over Na2 SO4 and concentrated on vacuum to give the product as an yellow oil.
Workup
- customthe dry ice/acetone bath was removed
- customto slowly reach 0° C
- customAt this temperature, the reaction mixture was quenched by addition of 25 ml of H2O
- extractionthe mixture was extracted twice with Et2O
- washthe organic layers were washed with brine
- customdried over Na2 SO4
- concentrationconcentrated on vacuum
Sources & evidence
- ORD record
- ord-b740e731a3434dd69a2c20f2e0c6649f
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748435B2
Reaction notes
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