Hydrochloric Acid → (S)-3-Methoxy-5-(2-methylpyrrolidin-1-YL)aniline

HRID 1410109

반응식

HRID 1410109 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1.Cl>O1CCOCC1.O.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])[CH:4]=1

참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 68379376(S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine

생성물 1

HCID 68379440(S)-3-Methoxy-5-(2-methylpyrrolidin-1-YL)aniline수율 72%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a suspension of (S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine (430 mg, 1.82 mmol) and Zinc (1.18 g, 18.2 mmol) in dioxane (20 mL) and H2O (10 mL) was added dropwise conc. HCl (1.8 mL) at room temperature, and the mixture was stirred for 2 h. The reaction mixture was filtered and the filtrate was adjusted to pH˜8 by the addition of solid NaHCO3, and then extracted with ethyl acetate (50 mL). The organic layer was dried with Na2SO4, concentrated and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to afford (S)-3-methoxy-5-(2-methylpyrrolidin-1-yl)benzenamine (269 mg, 72%) as yellow oil. LC-MS: 207 [M+H]+, tR=1.193 min.

후처리

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was adjusted to pH˜8 by the addition of solid NaHCO3
  3. extractionextracted with ethyl acetate (50 mL)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1)

출처 및 근거

ORD 기록
ord-f8d915773dc9436199ac78d19d08a571
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921383B2

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