Hydrochloric Acid → {3-[(Cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methanol

HRID 1710858ノート

反応式

HRID 1710858 の反応式
[CH:1]1([CH2:6][N:7]([CH2:21][CH3:22])[C:8]2[C:9]([CH2:16][O:17]COC)=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[OH-].[Na+]>O1CCOCC1.O>[CH:1]1([CH2:6][N:7]([CH2:21][CH3:22])[C:8]2[C:9]([CH2:16][OH:17])=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67242952N-(cyclopentylmethyl)-N-ethyl-6-methoxy-2-[(methoxymethoxy)methyl]pyridin-3-amine

生成物 1

HCID 67243028{3-[(Cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methanol収率 94%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

A solution of N-(cyclopentylmethyl)-N-ethyl-6-methoxy-2-[(methoxymethoxy)methyl]pyridin-3-amine (8.39 g, 27.2 mmol) in a mixture of dioxane (400 mL) and water (100 mL) was added dropwise with concentrated hydrochloric acid (20 mL), and the mixture was stirred at 50° C. for 19 hours. The reaction mixture was made basic by adding aqueous sodium hydroxide, and extracted with ethyl acetate. The organic layers were combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to obtain {3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methanol (6.72 g, 94%) as pale yellow oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

出典と根拠

ORDレコード
ord-dee0964a38b54717b934afb2f4980471
出典データセット
uspto-grants-2010_09
特許番号
US07790737B2

反応ノート

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