Ethyl Acetate → HCID 66755141, compound
Reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[O:13]=[C:14]1[CH2:31][CH2:30][C:17]2([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH2:16][CH2:15]1.C(OCC)(=O)C>C(OCC)C.O>[OH:13][C:14]1([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:31][CH2:30][C:17]2([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19][CH2:18]2)[CH2:16][CH2:15]1Participants
Conditions
- Temperature
- -78 °C
Procedure
3-Bromopyridine (22.47 mmol, 2 eq) was dissolved in diethyl ether (10 ml) and the solution was added dropwise to a solution of n-BuLi (24.7 mmol, 2.2 eq) in diethyl ether (70 ml) at −78° C. The resulting mixture was stirred for 30 min. tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (for the synthesis see above) (11.23 mmol, 1 eq.) was dissolved in diethyl ether (10 ml), the solution was slowly added, and the reaction mixture was then stirred at −78° C. for 1 h. The reaction mixture was warmed to room temperature, ethyl acetate (150 ml) and water (80 ml) were added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×70 ml) and the combined organic phases were dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography (2% methanol in methylene chloride). Yield: 19%
Workup
- additionthe solution was slowly added
- temperatureThe reaction mixture was warmed to room temperature
- customthe phases were separated
- extractionThe aqueous phase was extracted with ethyl acetate (2×70 ml)
- dry with materialthe combined organic phases were dried over magnesium sulfate
- concentrationconcentrated
- customThe crude product was purified by column chromatography (2% methanol in methylene chloride)
Sources & evidence
- ORD record
- ord-ce9e725c97f6499aaec9aa56d9212f52
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119805B2
Reaction notes
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