Acetic Acid → tert-Butyl 2-[3-[N-(3-hydroxypropyl)aminomethyl]phenoxy]butyrate

HRID 350847노트

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HRID 350847 반응식
[CH:1]([C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][CH:7]([CH2:15][CH3:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.[NH2:20][CH2:21][CH2:22][CH2:23][OH:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[OH:24][CH2:23][CH2:22][CH2:21][NH:20][CH2:1][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][CH:7]([CH2:15][CH3:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 90863-Amino-1-propanolHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21090531Tert-butyl 2-(3-formylphenoxy)butyrate

생성물 1

HCID 21090533tert-Butyl 2-[3-[N-(3-hydroxypropyl)aminomethyl]phenoxy]butyrate수율 33.3%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

tert-Butyl 2-(3-formylphenoxy)butyrate (105.1 mg, 0.42 mmol) was dissolved in chloroform (10 ml) at room temperature, and thereto were added 3-amino-1-propanol (0.04 ml, 0.47 mmol), sodium triacetoxyborohydride (134.6 mg, 0.63 mmol) and acetic acid (0.03 ml, 0.51 mmol) in sequential order at the same temperature, and then stirred at room temperature for 24 hours. The reaction mixture was added to a saturated aqueous sodium hydrogencarbonate solution and thereafter extracted by chloroform, to obtain an organic layer. The extracted organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressured. The resultant substance was purified by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound was obtained as a colorless oil (43.3 mg, 33.3%).

후처리

  1. extractionextracted by chloroform
  2. customto obtain an organic layer
  3. washThe extracted organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressured
  6. customThe resultant substance was purified by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound

출처 및 근거

ORD 기록
ord-04c9ac37f7034908adec7a5aa6165d83
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183295B2

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