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

HRID 906322노트

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HRID 906322 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-319cab7f09444be4bcd1bfb8d0d19a03
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012989B2

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