Sodium Hydroxide → 1-(Cyclohexylamino)-1-(hydroxymethyl)cyclopentane

HRID 276258

反応式

HRID 276258 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:11]1[C:15]2([NH:24][C:18]3([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[O:17][CH2:16]2)[CH2:14][CH2:13][CH2:12]1.[OH-].[Na+]>C1COCC1.O>[CH:18]1([NH:24][C:15]2([CH2:16][OH:17])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 1831620513-Oxa-6-azadispiro[4.1.5.2]tetradecaneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 183161421-(Cyclohexylamino)-1-(hydroxymethyl)cyclopentane収率 79%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
20 °C

実験手順

To a solution of LiAlH4 (0.93 g, 24.4 mmol) and AlCl3 (3.24 g, 24.4 mmol) in THF at 4° C. was added dropwise a solution of 14-aza-7-oxadispiro[4.2.5.1]tetradecane (2.38 g, 12,2 mmol) in THF (15 mL). The resulting mixture was warmed to 20° C. and stirred for 45 min., then cooled to 4° C. Water (5 mL) was slowly added to quench the reaction and a 1N NaOH solution (85 mL) was added to dissolve the resulting solids. The resulting solution was extracted with Et2O (200 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield 1-(cyclohexylamino)-1-(hydroxymethyl)cyclopentane 1.89 g (79%): GC-MS m/z 197 (M+).

後処理

  1. temperaturecooled to 4° C
  2. customto quench
  3. customthe reaction
  4. dissolutionto dissolve the resulting solids
  5. extractionThe resulting solution was extracted with Et2O (200 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6e68bfb8a2134a28b6bf190ddde2c6b9
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

関連ノート

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