Water → (2R)-2-amino-2-cyclohexylethan-1-ol

HRID 1848042노트

반응식

HRID 1848042 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]1[CH2:12][CH2:11][CH:10]([C@@H:13]([NH2:17])[C:14](O)=[O:15])[CH2:9][CH2:8]1.O.[OH-].[Na+]>C1COCC1>[NH2:17][C@H:13]([CH:10]1[CH2:11][CH2:12][CH2:7][CH2:8][CH2:9]1)[CH2:14][OH:15]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 736849Cyclohexylglycine, (R)-HCID 21226445Aluminium lithium hydride

생성물 1

HCID 13617488(2R)-2-amino-2-cyclohexylethan-1-ol수율 43.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

To a stirred mixture of LiAlH4 (724 mg, 19.08 mmol) in anhydrous THF (20 mL) at rt was added portionwise 2-cyclohexyl-D-glycine (1 g, 6.36 mmol). The mixture was heated at 80° C. for 4 h. The mixture was cooled to 0° C. and then water (1 mL), 1M aq NaOH (1 mL), and water (3 mL) were added sequentially. The mixture was filtered and the filtrate was partitioned between a mixture of DCM, 1M aq NaOH, and saturated aq sodium potassium tartrate. The organic layer was separated and further washed with 1M aq NaOH. The organic was separated, dried over MgSO4, filtered, and concentrated under reduced pressure to afford (R)-2-amino-2-cyclohexylethanol (400 mg) which was not purified further. LCMS (ESI) m/z 144 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationThe mixture was filtered
  3. customthe filtrate was partitioned between a mixture of DCM, 1M aq NaOH, and saturated aq sodium potassium tartrate
  4. customThe organic layer was separated
  5. washfurther washed with 1M aq NaOH
  6. customThe organic was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-83cde45171ba40aca2a6328d929b0118
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952058B2

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