Water → {1-Azabicyclo[3.2.1]octan-5-yl}methanol

HRID 5362

反応式

HRID 5362 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.C([O:14][C:15]([C:17]12[CH2:24][N:21]([CH2:22][CH2:23]1)[CH2:20][CH2:19][CH2:18]2)=O)C.O.[OH-].[Na+]>O1CCCC1>[N:21]12[CH2:24][C:17]([CH2:15][OH:14])([CH2:23][CH2:22]1)[CH2:18][CH2:19][CH2:20]2

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 15663615Ethyl 1-azabicyclo[3.2.1]octane-5-carboxylateHCID 68718528lithium aluminium hydride THF

生成物 1

HCID 19795992{1-Azabicyclo[3.2.1]octan-5-yl}methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A cooled (0° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (55 mL, 55 mmol) under nitrogen was treated dropwise with a solution of 1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester (9.17 g, 50 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 30 minutes at room temperature, refluxed for one hour, and cooled (0° C.). In sequence, water (2.1 mL), 15% sodium hydroxide solution (2.1 mL) and water (6.3 mL) were carefully added dropwise, and the mixture was filtered through Celite (the solid was washed with tetrahydrofuran) and concentrated in vacuo to afford 6.50 g (92%) of viscous, colorless oil, which can be used as is or can be solidified on cooling; mp 44°-47° C.

後処理

  1. temperaturerefluxed for one hour
  2. temperaturecooled (0° C.)
  3. filtrationthe mixture was filtered through Celite (the solid
  4. washwas washed with tetrahydrofuran) and
  5. concentrationconcentrated in vacuo
  6. customto afford 6.50 g (92%) of viscous, colorless oil, which
  7. temperatureon cooling

出典と根拠

ORDレコード
ord-3f6f7292f4214dacbbc44e42e9963d38
出典データセット
uspto-grants-1993_09
特許番号
US05244907

関連ノート

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