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

HRID 1486248ノート

反応式

HRID 1486248 の反応式
[NH2:1][C:2]([CH3:15])([CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]#[N:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:8]([O:7][CH2:6][CH2:5][C:2]([CH3:15])([NH2:1])[CH2:3][NH2:4])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 583790832-Amino-4-(benzyloxy)-2-methylbutanonitrile

生成物 1

HCID 90114043rac-4-(Benzyloxy)-2-methylbutane-1,2-diamine収率 58.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

0.5 g (2.45 mmol) of rac-2-amino-4-(benzyloxy)-2-methylbutanonitrile from Example 32A in 25 ml of dry THF were admixed under argon at 0° C. with 1.59 ml (1.59 mmol) of lithium aluminium hydride (1 N solution in diethyl ether). The reaction solution was first stirred at 0° C. for 30 min and then stirred for 1 h, gradually coming to room temperature. Then 245 μl of water, 245 μl of 2 N aqueous sodium hydroxide solution and 490 μl of water were added cautiously. The precipitate was filtered off and washed with THF and methanol, the filtrate was concentrated and the residue was purified by means of silica gel chromatography (eluent:dichloromethane/2 N ammonia in methanol=20/1, isocratic). 0.30 g of the target compound (96% purity, 57% of theory) was obtained.

後処理

  1. stirringstirred for 1 h
  2. customgradually coming to room temperature
  3. filtrationThe precipitate was filtered off
  4. washwashed with THF and methanol
  5. concentrationthe filtrate was concentrated
  6. customthe residue was purified by means of silica gel chromatography (eluent:dichloromethane/2 N ammonia in methanol=20/1, isocratic)

出典と根拠

ORDレコード
ord-1cf4e6d3016c48b88a4c8cd9f39b4812
出典データセット
uspto-grants-2016_08
特許番号
US09422285B2

反応ノート

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