Triethylamine → Tert-butyl 3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[CH3:57][NH:58][O:59][CH3:60]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([N:58]([O:59][CH3:60])[CH3:57])=[O:16])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cold (0° C.) solution of 1-(tert-butoxycarbonyl)-3-piperidine carboxylic acid (7.000 g, 30.531 mmol) in dichloromethane (200 mL) including triethylamine (4.681 mL, 33.584 mmol) were added benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (15.885 g, 30.531 mmol), N,O-dimethylhydroxyamine (3.276 g, 33.584 mmol) and triethylamine (4.255 mL, 30.531 mmol) successively. The mixture was allowed to warm to room temperature, and the stirring was continued for 12 hrs. The reaction mixture was diluted with dichloromethane and washed with an aqueous 1N HCl solution, saturated aqueous NaHCO3 solution, and brine, successively. The organic phase was dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=10/1-9/1) to give 3-{[methoxy(methyl)amino]carbonyl}-1-piperidine-carboxylic acid tert-butyl ester as a white solid. (8.050 g, yield; 96%)
Workup
- washwashed with an aqueous 1N HCl solution, saturated aqueous NaHCO3 solution, and brine
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe resulting residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=10/1-9/1)
Sources & evidence
- ORD record
- ord-7d1ebc80eebb4e4c8d11712852d9f8f1
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562811B1
Reaction notes
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