Water → {1-Azabicyclo[3.3.1]nonan-5-yl}methanamine

HRID 5366

反応式

HRID 5366 の反応式
[N:1]12[CH2:9][C:5]([C:10]([NH2:12])=O)([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.O.[OH-].[Na+]>O1CCCC1.CCOCC>[N:1]12[CH2:9][C:5]([CH2:10][NH2:12])([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2

参加物

7

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 197959811-Azabicyclo[3.3.1]nonane-5-carboxamideHCID 68718528lithium aluminium hydride THF

生成物 1

HCID 19795986{1-Azabicyclo[3.3.1]nonan-5-yl}methanamine収率 77%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A suspension of 1-azabicyclo[3.3.1]nonane-5-carboxamide (1.80 g, 10.7 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated (via syringe) with 1.0N lithium aluminum hydride/tetrahydrofuran (25 mL, 25 mmol), and the mixture was refluxed for 4 hours and cooled (0° C.). The mixture was treated carefully dropwise sequentially with water (1 mL), 15% sodium hydroxide (1 mL), and water (3 mL). Ether (50 mL) was added, the mixture was filtered through Celite, and the filter cake was washed with ether. The filtrate was concentrated in vacuo to afford 1.27 g (77%) of colorless oil.

後処理

  1. temperaturethe mixture was refluxed for 4 hours
  2. filtrationthe mixture was filtered through Celite
  3. washthe filter cake was washed with ether
  4. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-0445a3a91b3b46b584c36be6a9648625
出典データセット
uspto-grants-1993_09
特許番号
US05244907

関連ノート

読み込み中…