2-Methoxyethylamine → (S)-N-(2-methoxyethyl)piperidine-3-carboxamide

HRID 625249ノート

反応式

HRID 625249 の反応式
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]

参加物

7

反応物 4

HCID 80182-MethoxyethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6951168(3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acid

生成物 1

HCID 28162916(S)-N-(2-methoxyethyl)piperidine-3-carboxamide収率 100%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  1. customthe solvent was evaporated at reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was sequentially washed with water
  4. dry with materialThe solution was dried (Na2SO4)
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in a 4 M solution of HCl in dioxane
  7. customAfter 1 h the mixture was evaporated

出典と根拠

ORDレコード
ord-826cf19df4d14ff99e2ab61b5cfab288
出典データセット
uspto-grants-2016_04
特許番号
US09301951B2

反応ノート

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