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

HRID 1848057노트

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HRID 1848057 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 22379486(1-(Aminomethyl)cyclohexyl)methanol수율 58.4%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-40ab976a1e3a4bc590e572b67738b5a9
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952058B2

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