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

HRID 1040444노트

반응식

HRID 1040444 반응식
[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]

참가 물질

6

반응물 3

HCID 962WaterHCID 232981494-[(tert-Butoxycarbonylamino)methyl]-2-cyanopyridineHCID 178418443HCID 178418443, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-1c583627cf7048e5bf7e3b896e4ee8c1
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552205B2

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