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

HRID 1500886ノート

反応式

HRID 1500886 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 674652054-(Benzylamino)-1-methylcyclohexanol収率 81.2%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-85631cfc45d64bad8f263c7123fb1cbe
出典データセット
uspto-grants-2015_12
特許番号
US09206191B2

反応ノート

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