Tert-Butylamine → HCID 89422940、化合物

HRID 1481680ノート

反応式

HRID 1481680 の反応式
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](=O)[CH2:13][CH2:14][CH3:15])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[CH3:17][C:18]([NH2:21])([CH3:20])[CH3:19]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:17][C:18]([N:21]=[C:12]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]2)[CH2:13][CH2:14][CH3:15])([CH3:20])[CH3:19]

参加物

5

反応物 2

HCID 6385Tert-ButylamineHCID 39104401HCID 39104401、化合物

生成物 1

HCID 89422940HCID 89422940、化合物

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)butan-1-one (2.94 g, 13.5 mmol) in CH2Cl2 (14 mL) was added 2-methylpropan-2-amine (5.7 mL, 54.2 mmol, 4.0 eq). The mixture was cooled to 0° C. before TiCl4 (1.0M in CH2Cl2, 8.8 mL, 8.8 mmol, 0.65 eq) was added via syringe pump over 30 min. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL) then extracted by CH2Cl2 (5×25 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was carried over to next step without further purification. LC-MS 273.1 [M+H]+, RT 0.65 min. (1 min Method).

後処理

  1. additionwas added via syringe pump over 30 min
  2. customThe reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL)
  3. extractionthen extracted by CH2Cl2 (5×25 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationthen concentrated

出典と根拠

ORDレコード
ord-9b2bb029956d44299353139e2611a6a5
出典データセット
uspto-grants-2016_08
特許番号
US09409905B2

反応ノート

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