2-Methoxyethylamine → (S)-N-(2-methoxyethyl)piperidine-3-carboxamide
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=O)[CH2:9]1)=O)(C)(C)C.[CH3:17][O:18][CH2:19][CH2:20][NH2:21].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>ClCCl.C(N(CC)CC)C>[CH3:17][O:18][CH2:19][CH2:20][NH:21][C:14]([C@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)=[O:16]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A 0° C. solution of 500 mg of (S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid, 328 mg of 2-methoxyethylamine, 736 mg of HOBt, and 1.82 mL of triethylamine in 9 mL of dichloromethane was treated with 836 mg of EDC.HCl. The mixture was stirred at 25° C. overnight and the solvent was evaporated at reduced pressure. The residue was dissolved in ethyl acetate, and the solution was sequentially washed with water, an aqueous solution of citric acid, an aqueous sodium bicarbonate solution, and brine. The solution was dried (Na2SO4) and the solvent was evaporated. The residue was dissolved in a 4 M solution of HCl in dioxane. After 1 h the mixture was evaporated to give 406 mg of the product.
Workup
- customthe solvent was evaporated at reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate
- washthe solution was sequentially washed with water
- dry with materialThe solution was dried (Na2SO4)
- customthe solvent was evaporated
- dissolutionThe residue was dissolved in a 4 M solution of HCl in dioxane
- customAfter 1 h the mixture was evaporated
Sources & evidence
- ORD record
- ord-826cf19df4d14ff99e2ab61b5cfab288
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09301951B2
Reaction notes
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