Tert-Butylamine → Tert-butylamino-pyridin-3-yl-acetic acid ethyl ester

HRID 352215ノート

反応式

HRID 352215 の反応式
[CH2:1]([O:3][C:4](=[O:13])[CH:5](Br)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

参加物

5

反応物 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetate

生成物 1

HCID 69850097Tert-butylamino-pyridin-3-yl-acetic acid ethyl ester収率 41.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Bromo-pyridin-3-yl-acetic acid ethyl ester (2.4 g; 9.8 mmol) was reacted in refluxing CH2Cl2, overnight with tert-butylamine (6.2 mL; 55.8 mmol; 6 equiv) and Et3N (2.8 mL; 19.6 mmol; 2 equiv). The reaction solution was evaporated to dryness, dissolved in CH2Cl2, washed six times with saturated NaHCO3 (aq), washed once with saturated NaCl (aq), dried with Na2SO4, filtered, and concentrated in vacuo. The resulting brown oil was purified with silica gel chromatography in a 6×8 cm glass column using a 30% EtOAc/hexanes (v/v) mobile phase. A total of 955 mg desired product was isolated (41% yield). MS(ES) calc'd: [M+H]+=237.1 m/z. Found: 237.1 m/z.

後処理

  1. customThe reaction solution was evaporated to dryness
  2. dissolutiondissolved in CH2Cl2
  3. washwashed six times with saturated NaHCO3 (aq)
  4. washwashed once with saturated NaCl (aq)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting brown oil was purified with silica gel chromatography in a 6×8 cm glass column

出典と根拠

ORDレコード
ord-3499288dff3147a4924a45c2b553ec54
出典データセット
uspto-grants-2004_06
特許番号
US06743794B2

反応ノート

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