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Tetrahydrofuran → N-(2'-Cyanobiphenyl-4-ylmethyl)-N-methoxycarbonylmethyl-amine

HRID 1609175
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반응식

HRID 1609175 반응식
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)#[N:2].Cl.[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH2:22].O1CCCC1.C([BH3-])#N.[Na+]>CO>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][NH:22][CH2:21][C:20]([O:19][CH3:18])=[O:23])=[CH:13][CH:14]=1)#[N:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 122755Glycine methyl ester hydrochlorideHCID 13940624'-Formyl-[1,1'-biphenyl]-2-carbonitrileHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 21840383N-(2'-Cyanobiphenyl-4-ylmethyl)-N-methoxycarbonylmethyl-amine

시약·촉매·용매 1

HCID 887Methanol
용매

실험 절차

A mixture of 2.0 g of 2'-cyano-4-formyl-biphenyl, 1.22 g of 2-aminoethanoic acid methyl ester hydrochloride, 9.6 g of molecular sieve 5 A and 26 ml of tetrahydrofuran is stirred at room temperature for 36 hours and then cooled to 0° to 5°. 680 mg of sodium cyanoborohydride (90%) dissolved in 4.8 ml of methanol are added. The mixture is stirred at room temperature for 24 hours and then concentrated in vacuo. The crude product is purified by means of flash chromatography (180 g of silica gel; ethyl acetate/petroleum ether=1:1). 1H-NMR (DMSO-d6): 3.63 ppm (s, 3 H); 3.79 ppm (s, 2H); 7.4 to 8.0 ppm (m, 10H); 2.6 ppm (1H).

후처리

  1. temperaturecooled to 0° to 5°
  2. additionare added
  3. stirringThe mixture is stirred at room temperature for 24 hours
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by means of flash chromatography (180 g of silica gel; ethyl acetate/petroleum ether=1:1)

출처 및 근거

ORD 기록
ord-fd7a6dea757947158034e14c5dfd8b8c
출처 데이터셋
uspto-grants-1995_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05399578

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