Triethylamine → 4-(Methoxymethylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](CC2C=CC=CC=2)([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.Cl.CN[O:31][CH3:32].[CH2:33]([N:35](CC)CC)C>C1COCC1.C(Cl)Cl.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:35][CH2:33][O:31][CH3:32])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a stirring solution of 4-benzylpiperidine-1,4-dicarboxylic acid tert-butyl ester (12.5 mmol, 4.0 g) in THF (60 mL) was added thionyl chloride (13.8 mmol, 1.64 g) and pyridine (0.2 mL). The reaction was stirred at r.t. for 1 h. The reaction was then evaporated under reduced pressure and the residue taken up in CH2Cl2 (50 mL). To this solution was added N,O-Dimethylhydroxylamine hydrochloride (13.8 mmol,1.35 g) and triethylamine (25.0 mmol, 2.53 g). The reaction was stirred at room temperature for 1 h. The reaction was then diluted with CH2Cl2 (100 mL) and washed with 10% KHSO4. (100 mL) and saturated sodium bicarbonate (100 mL). The organic layers were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was evaporated from ethyl ether:hexanes to give 4.14 g of the title compound as a white solid.
Workup
- customThe reaction was then evaporated under reduced pressure
- stirringThe reaction was stirred at room temperature for 1 h
- washwashed with 10% KHSO4
- washThe organic layers were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customevaporated under reduced pressure
- customThe residue was evaporated from ethyl ether
Sources & evidence
- ORD record
- ord-864a017eb15740edb120f754c7d64b3e
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06083949
Reaction notes
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