3-Ethoxy-4-methoxybenzaldehyde → 3-(3-Ethoxy-4-methoxy-benzylamino)-propionic acid ethyl ester

HRID 275893

반응식

HRID 275893 반응식
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])[CH3:3].[CH2:10]([O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:16]=O)[CH3:11].C([BH3-])#N.[Na+]>C(O)C>[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH:8][CH2:16][C:15]1[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:13]([O:12][CH2:10][CH3:11])[CH:14]=1)[CH3:3]

참가 물질

5

반응물 3

HCID 2447283-Ethoxy-4-methoxybenzaldehydeHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydride2회

생성물 1

HCID 538585443-(3-Ethoxy-4-methoxy-benzylamino)-propionic acid ethyl ester수율 39.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of β-alanine ethyl ester hydrochloride (1.6 g), 3-ethoxy-4-methoxybenzaldehyde (1.8 g), sodium cyanoborohydride (0.42 g) and powdered 3Å molecular seives (2.5 g) in ethanol (25 ml) was stirred at ambient temperature for 24 hours. A further aliquot of sodium cyanoborohydride (0.42 g) was added and stirring was continued for a further 24 hours. The reaction mixture was filtered and the filtrate was evaporated. The residue was treated with ethyl acetate (100 ml) and the solution was washed with 10% aqueous potassium carbonate (50 ml), then twice with water (25 ml), then with brine (25 ml), then dried over magnesium sulphate and then evaporated. The residual oil was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95:5, v/v) to give the title compound as a colourless oil (1.1 g).

후처리

  1. stirringstirring
  2. waitwas continued for a further 24 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated
  5. additionThe residue was treated with ethyl acetate (100 ml)
  6. washthe solution was washed with 10% aqueous potassium carbonate (50 ml)
  7. dry with materialtwice with water (25 ml), then with brine (25 ml), then dried over magnesium sulphate
  8. customevaporated
  9. additionThe residual oil was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95:5

출처 및 근거

ORD 기록
ord-63a853df8ade4b968ea2376812013b75
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352977B1

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