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

HRID 1609175Notes

Reaction equation

HRID 1609175 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-fd7a6dea757947158034e14c5dfd8b8c
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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