Acetic Acid → 4-(Benzylamino)-1-methylcyclohexanol

HRID 1500886노트

반응식

HRID 1500886 반응식
[OH:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl>[CH2:10]([NH:17][CH:5]1[CH2:6][CH2:7][C:2]([CH3:9])([OH:1])[CH2:3][CH2:4]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 285394-Hydroxy-4-methylcyclohexanoneHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 674652054-(Benzylamino)-1-methylcyclohexanol수율 81.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a mixture of 4-hydroxy-4-methylcyclohexanone (4.1 g, 32.0 mmol) and benzyl amine (6.8 g, 64.0 mmol) in 1,2-dichloroethane (120 mL) was added acetic acid (3.84 g, 64.0 mmol). After the resulting mixture was stirred at RT for 2 hours, the mixture was added NaBH(OAc)3 (13.6 g, 64.0 mmol). The resulting mixture was then stirred at RT overnight. After the reaction was completed, the mixture was basified to pH 11 by addition of 2 N NaOH. The separated organic layer was concentrated in vacuo and the residue was purified by column chromatography on silica gel (MeOH:DCM=3:100 to 1:10) to afford 4-(benzylamino)-1-methylcyclohexanol as a white solid (5.7 g, yield: 80.0%).

후처리

  1. stirringThe resulting mixture was then stirred at RT overnight
  2. concentrationThe separated organic layer was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (MeOH:DCM=3:100 to 1:10)

출처 및 근거

ORD 기록
ord-85631cfc45d64bad8f263c7123fb1cbe
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206191B2

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