Triethylamine → tert-Butyl 2-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][NH:19][O:20][CH3:21].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[CH3:18][N:19]([O:20][CH3:21])[C:14]([CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-t-butoxycarbonylpiperidine-2-carboxylic acid (2.29 g) in methylene chloride (30 mL) were added N,O-dimethylhydroxyamine hydrochloride (1.17 g), benzotriazol-1-yloxy-tris(dimethylamino)phosphoniumhexafluorophosphate (4.87 g, BOP reagent) and triethylamine (4.88 mL) and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated. The residue was diluted with ethyl acetate. The diluted solution was washed water, 1N hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution and brine sequentially, dried over anhydrous sodium sulfate and concentrated to give the title compound (2.59 g) having the following physical data.
Workup
- concentrationThe reaction mixture was concentrated
- additionThe residue was diluted with ethyl acetate
- washThe diluted solution was washed water, 1N hydrochloric acid, water
- dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine sequentially, dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e0c68ab0693c4c159ded5b942cddad0b
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07402580B2
Reaction notes
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