Benzylamine → {3-[2-(Benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester

HRID 1969021노트

반응식

HRID 1969021 반응식
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH:19]=O)[CH:6]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][NH:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=1

참가 물질

6

반응물 3

HCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 58237467[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester

생성물 1

HCID 58288498{3-[2-(Benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 6344Dichloromethane용매

실험 절차

[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester (0.151 g, 0.43 mmol), benzylamine (0.05 mL, 0.48 mmol), and sodium cyanoborohydride (0.041 g, 0.65 mmol) were combined in CH2Cl2 (3 mL). Acetic acid (2 drops) was added, and the reaction was stirred overnight at room temperature. The mixture was partitioned between CH2Cl2 and saturated aqueous NaHCO3, and the aqueous layer was separated and extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated, and the residue was purified by silica gel chromatography (10-30% EtOAc in hexanes) to give the title compound.

후처리

  1. customThe mixture was partitioned between CH2Cl2 and saturated aqueous NaHCO3
  2. customthe aqueous layer was separated
  3. extractionextracted twice with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (10-30% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-90aad6fb93d84d80941b9b3fcf7fac4f
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426449B2

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