Sodium cyanoborohydride → HCID 11256259, compound

HRID 2238602Notes

Reaction equation

HRID 2238602 reaction equation
Cl.[CH3:2][NH:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].C([BH3-])#N.[Na+].[C:13]1([CH2:19][CH2:20][CH:21]2[C:25]3[CH:26]=[C:27]([CH:30]=O)[CH:28]=[CH:29][C:24]=3[O:23][CH2:22]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:20]([CH:21]1[C:25]2[CH:26]=[C:27]([CH2:30][NH:6][CH:5]([CH3:7])[C:4]([NH:3][CH3:2])=[O:8])[CH:28]=[CH:29][C:24]=2[O:23][CH2:22]1)[CH2:19][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 18595779(2S)-2-amino-N-methylpropanamide hydrochlorideHCID 57445526HCID 57445526, compound

Product 1

HCID 11256259HCID 11256259, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of N-methyl-alaninamide hydrochloride (0.50 g, 3.61 mmol) in methanol (10 ml), in the presence of molecular sieves (1.00 g), sodium cyanoborohydride (0.36 g, 5.69 mmol) and a solution of 3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-carboxaldehyde (0.90 g, 3.61 mmol) in methanol (10 ml) were added at room temperature. The reaction mixture was kept under stirring and an argon atmosphere for 12 h. Then, the solvent was evaporated under vacuum and the residue was purified by flash chromatography on silica gel (ethyl acetate/methanol=98/2) affording 0.93 g of title compound (77% yield).

Workup

  1. customThen, the solvent was evaporated under vacuum
  2. customthe residue was purified by flash chromatography on silica gel (ethyl acetate/methanol=98/2)

Sources & evidence

ORD record
ord-5165846ba05a47a0b3d46687e1b736ea
Source dataset
uspto-grants-2010_05
Patent number
US07718815B2

Reaction notes

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