Acetic Acid → {2-[2,2-Dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine

HRID 76221

반응식

HRID 76221 반응식
[CH3:1][C:2]1([CH3:18])[CH2:7][C:6]([CH2:15][CH:16]=O)([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH2:5][CH2:4][O:3]1.[CH3:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH2:24].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:18])[CH2:7][C:6]([CH2:15][CH2:16][NH:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[C:20]([CH3:19])[CH:21]=2)([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH2:5][CH2:4][O:3]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 660153-MethylbenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866714262-[2,2-Dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde

생성물 1

HCID 68314021{2-[2,2-Dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde (61.6 mg, 0.25 mmol), 3-methylbenzylamine (63 μl, 0.5 mmol) and acetic acid (50 μl, 8.6 mmol) in CH2Cl2 (3 ml) was stirred at rt for 1 h before it adding sodium triacetoxyborohydride (106 mg, 0.50 mmol). The resulting mixture was stirred at rt for 18 h. The mix was concentrated and dissolved in MeOH and purified by HPLC to give {2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine as a white solid (35 mg, 40%, m/z: 352.3 [M+H]+ observed).

후처리

  1. stirringThe resulting mixture was stirred at rt for 18 h
  2. concentrationThe mix was concentrated
  3. dissolutiondissolved in MeOH
  4. custompurified by HPLC

출처 및 근거

ORD 기록
ord-a1af5ac96c35468a8bca66679b51e7de
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835488B2

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