Sodium Hydroxide → (1-(Aminomethyl)cyclohexyl)methanol

HRID 1848057ノート

反応式

HRID 1848057 の反応式
[C:1]([C:3]1([C:9](OC)=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1.C(Cl)Cl.O>[NH2:2][CH2:1][C:3]1([CH2:9][OH:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 9855836Potassium sodium tartarateHCID 11182833Methyl 1-cyanocyclohexane-1-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 22379486(1-(Aminomethyl)cyclohexyl)methanol収率 58.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of methyl 1-cyanocyclohexanecarboxylate (2 g, 11.96 mmol) in anhydrous THF (40 mL) at rt was added portionwise LiAlH4 (1.36 g, 35.88 mmol). The reaction vessel was sealed and the mixture was heated at 80° C. for 5 h. The mixture was cooled to 0° C. and water (1 mL), 1M aq NaOH (1 mL), and water (3 mL) were added sequentially. To the resulting mixture were added DCM and saturated aq sodium potassium tartrate, and the mixture was stirred for 3 h. The organic layer was separated and further washed with brine. The organic layer was separated, dried over MgSO4, filtered, and concentrated under reduced pressure to afford (1-(aminomethyl)cyclohexyl)methanol (1 g) which was not purified further. LCMS (ESI) m/z 144 (M+H)+.

後処理

  1. customThe reaction vessel was sealed
  2. temperatureThe mixture was cooled to 0° C.
  3. customThe organic layer was separated
  4. washfurther washed with brine
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-40ab976a1e3a4bc590e572b67738b5a9
出典データセット
uspto-grants-2015_02
特許番号
US08952058B2

反応ノート

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