Acetic Acid → 4-(Cyclopropylamino)cyclohexanol

HRID 509280

반응식

HRID 509280 반응식
O[CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH:9]1([NH2:12])[CH2:11][CH2:10]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.[OH-].[Na+]>ClCCCl>[CH:9]1([NH:12][CH:2]2[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]2)[CH2:11][CH2:10]1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 5437064-HydroxycyclohexanoneHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 674688554-(Cyclopropylamino)cyclohexanol수율 96.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

4-hydroxycyclohexanone (443 mg, 3.88 mmol) was dissolved in 1,2-dichloroethane (20 ml), followed by sequential addition of cyclopropylamine (0.295 ml, 4.27 mmol), NaBH(OAc)3 (1.3 g, 6.21 mmol), and acetic acid (0.2 ml, 3.88 mmol), and then the resulting mixture was stirred at room temperature under nitrogen stream for 13 hours. The resulting reaction liquid was neutralized by addition of 10% aqueous NaOH solution, and extracted with 10% MeOH/MC (15 ml×4). The organic layer was dried over anhydrous sodium sulfate, followed by filtration, concentration, and vacuum drying, to obtain 580 mg of yellow solid (96%).

후처리

  1. customThe resulting reaction liquid
  2. extractionextracted with 10% MeOH/MC (15 ml×4)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfollowed by filtration, concentration, and vacuum
  5. customdrying

출처 및 근거

ORD 기록
ord-9665846892b6482b9427b017797db0fe
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096571B2

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