Water → [2-(1-Amino-cyclopropyl)-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester

HRID 1040444ノート

反応式

HRID 1040444 の反応式
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]#[N:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([Mg]Br)[CH3:19].O>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2([NH2:16])[CH2:19][CH2:18]2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 962WaterHCID 232981494-[(tert-Butoxycarbonylamino)methyl]-2-cyanopyridineHCID 178418443HCID 178418443、化合物

生成物 1

HCID 67390399[2-(1-Amino-cyclopropyl)-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2-cyano-pyridin-4-ylmethyl)-carbamic acid tert-butyl ester (1.2 g, 5.1 mmol) in THF (100 mL) was added ethylmagnesium bromide (3 M, 3.3 mL, 10 mmol) and titanium isopropoxide (2.3 mL, 7.7 mmol). The reaction mixture was stirred at room temperature for 16 h. Water was added (5 mL) and the resulting solids filtered off. The organics were concentrated, then purified by flash chromatography on silica gel using 5-10% MeOH/CH2Cl2 to afford [2-(1-amino-cyclopropyl)-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester as a solid, m/z 264.4 [M+1]+.

後処理

  1. filtrationthe resulting solids filtered off
  2. concentrationThe organics were concentrated
  3. custompurified by flash chromatography on silica gel using 5-10% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-1c583627cf7048e5bf7e3b896e4ee8c1
出典データセット
uspto-grants-2013_10
特許番号
US08552205B2

反応ノート

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