Water → rac-4-(Benzyloxy)-2-methylbutane-1,2-diamine

HRID 2275860노트

반응식

HRID 2275860 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]([CH3:21])([CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]#[N:10].O.[OH-].[Na+]>C1COCC1>[CH2:14]([O:13][CH2:12][CH2:11][C:8]([CH3:21])([NH2:7])[CH2:9][NH2:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 583790832-Amino-4-(benzyloxy)-2-methylbutanonitrile

생성물 1

HCID 90114043rac-4-(Benzyloxy)-2-methylbutane-1,2-diamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Under argon and at 0° C., 1.59 ml (1.59 mmol) of lithium aluminium hydride (1 N solution in diethyl ether) were added to 0.5 g (2.45 mmol) of 2-amino-4-(benzyloxy)-2-methylbutanonitrile Example 260A in 25 ml of dry THF. The reaction solution was stirred first at 0° C. for 30 min and then for another 1 h whilst slowly warming to room temperature. 245 μl of water, 245 μl of 2 N aqueous sodium hydroxide solution and 490 μl of water were then added carefully. The precipitate was filtered off and washed with THF and methanol, the filtrate was concentrated and the residue was purified by silica gel chromatography (mobile phase: dichloromethane/2 N ammonia in methanol=20/1, isocratic). This gave 0.30 g of the target compound (96% pure, 57% of theory).

후처리

  1. temperaturefor another 1 h whilst slowly warming to room temperature
  2. filtrationThe precipitate was filtered off
  3. washwashed with THF and methanol
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by silica gel chromatography (mobile phase: dichloromethane/2 N ammonia in methanol=20/1, isocratic)

출처 및 근거

ORD 기록
ord-cca3bdc92ee940e8822ba1fd2d0d0e7b
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126998B2

반응 노트

불러오는 중…