Tetrahydrofuran → 1,1-Dimethylethyl 2-azabicyclo[3.1.0]hexane-2-carboxylate
Reaction equation
CN(CCN(C)C)C.C([Li])(CC)C.C1COCC1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29](Cl)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O.C(OCC)(=O)C>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]2[CH:27]1[CH2:28]2)=[O:25])([CH3:22])([CH3:21])[CH3:20]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
TMEDA (0.11 mL) was slowly added dropwise at −78° C. to a mixture of sec-butyllithium (1.4 M; 0.52 mL) and THF (1.8 mL). Then it was stirred for a further 30 min at −78° C. and then a solution of 4-chloro-piperidine-1-carboxylic acid tert-butyl ester (160 mg) in a little THF was slowly added dropwise. The reaction mixture was stirred for 2 h at −78° C., then it was allowed to return slowly to room temperature. Ethyl acetate and water were added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum.
Workup
- stirringThe reaction mixture was stirred for 2 h at −78° C.
- customto return slowly to room temperature
- extractionthe aqueous phase was extracted several times with ethyl acetate
- dry with materialdried over sodium sulfate
- customthe solvent was removed in vacuum
Sources & evidence
- ORD record
- ord-8ab4bb41937f4f1c8ee219a39df206b2
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822495B2
Reaction notes
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