Acetic Acid → N-(3-phenoxyphenyl)[[3-(1,1-dimethylethoxy)phenyl]methyl]amine

HRID 1017031

반응식

HRID 1017031 반응식
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[O:14]([C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C1COCC1.CCCCCC.C(OCC)(=O)C>[O:14]([C:21]1[CH:22]=[C:23]([NH:24][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:7]=2)[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 771353-PhenoxyanilineHCID 5049666Sodium triacetoxyborohydrideHCID 157122243-Tert-butoxybenzaldehyde

생성물 1

HCID 10936948N-(3-phenoxyphenyl)[[3-(1,1-dimethylethoxy)phenyl]methyl]amine수율 41.6%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

EX-654B) The 3-t-butoxybenzaldehyde (0.585 g, 3.27 mmol) product from EX-654A and 3-phenoxyaniline (0.595 g, 3.21 mmol) were combined in 50 mL of THF, then solid NaBH(OAc)3 (0.860 g, 4.06 mmol) was added, and the mixture was stirred until uniform. Acetic acid (0.2 g, 3.33 mmol) was added, and the mixture was stirred at room temperature for 4 h, then quenched with 5% aq. NaHCO3. The aqueous layer was separated and extracted twice with ether. The combined ether layers were washed with water and brine, dried over MgSO4, filtered, and evaporated to give 1.29 g (115%) of crude product as a brown oil. Chromatography on silica gel eluting with 0-10% ethyl acetate in hexane gave 464 mg (40%) of the desired N-(3-phenoxyphenyl)[[3-(1,1-dimethyl-ethoxy)phenyl]methyl]amine product as a colorless oil, pure by TLC. MS m/z=347 [M+].

후처리

  1. stirringthe mixture was stirred at room temperature for 4 h
  2. customquenched with 5% aq. NaHCO3
  3. customThe aqueous layer was separated
  4. extractionextracted twice with ether
  5. washThe combined ether layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give 1.29 g (115%) of crude product as a brown oil

출처 및 근거

ORD 기록
ord-da176ce507d548d489cd13a5020de814
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06476057B1

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