Sodium cyanoborohydride → 3-{4-[(4-Cyclohex-1-enylphenylamino)methyl]benzoylamino}propionic acid methyl ester

HRID 49549Notes

Reaction equation

HRID 49549 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1.[C:18]1([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:28][C:27]2[CH:29]=[CH:30][C:24]([C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=3)=[CH:25][CH:26]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 126688602',3',4',5'-Tetrahydro-[1,1'-biphenyl]-4-amineHCID 161003253-(4-Formylbenzoylamino)propionic acid methyl ester

Product 1

HCID 207761293-{4-[(4-Cyclohex-1-enylphenylamino)methyl]benzoylamino}propionic acid methyl esterYield 21.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-(4-Formylbenzoylamino)propionic acid methyl ester (10 g, 42.5 mmol) was dissolved in methanol (100 ml). With mechanical stirring a solution of 4-cyclohex-1-enylaniline (7.4 g, 42.5 mmol) in methanol (15 ml) was added and the resulting suspension was stirred at room temperature for 2.5 hours. Sodium cyano borohydride (4.01 g, 63.8 mmol) was added in portions and the resulting mixture was stirred at room temperature for 4 days. Filtration afforded 7.1 g of a solid and recrystallisation from methanol afforded 3.55 g of 3-{4-[(4-cyclohex-1-enylphenylamino)methyl]benzoylamino}propionic acid methyl ester.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature for 4 days
  3. filtrationFiltration
  4. customafforded
  5. custom7.1 g of a solid and recrystallisation from methanol

Sources & evidence

ORD record
ord-82a4b8ccef884dedbb43fd7771005a54
Source dataset
uspto-grants-2004_03
Patent number
US06706744B2

Reaction notes

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