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

HRID 1410109

反応式

HRID 1410109 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f8d915773dc9436199ac78d19d08a571
出典データセット
uspto-grants-2014_12
特許番号
US08921383B2

関連ノート

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