Sodium cyanoborohydride → HCID 11427314, compound

HRID 2238603Notes

Reaction equation

HRID 2238603 reaction equation
Cl.[CH3:2][NH:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].C([BH3-])#N.[Na+].[CH2:13]([CH:20]1[C:24]2[CH:25]=[C:26]([CH:29]=O)[CH:27]=[CH:28][C:23]=2[O:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO>[CH2:13]([CH:20]1[C:24]2[CH:25]=[C:26]([CH2:29][NH:6][CH:5]([CH3:7])[C:4]([NH:3][CH3:2])=[O:8])[CH:27]=[CH:28][C:23]=2[O:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 18595779(2S)-2-amino-N-methylpropanamide hydrochlorideHCID 23081980HCID 23081980, compound

Product 1

HCID 11427314HCID 11427314, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (S)-N-methyl-alaninamide hydrochloride (0.50 g, 3.6 mmol) in methanol (10 ml), in the presence of molecular sieves (1.00 g), sodium cyanoborohydride (0.44 g, 6.9 mmol) and a solution of 3-benzyl-2,3-dihydro-1-benzofuran-5-carbaldehyde (0.75 g, 3.6 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) affording 0.58 g of title compound (50% yield).

Workup

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

Sources & evidence

ORD record
ord-ca04dc43a35246bebe3015f5f409b7d5
Source dataset
uspto-grants-2010_05
Patent number
US07718815B2

Reaction notes

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