Sodium triacetoxyborohydride → HCID 86637893, compound

HRID 2389319Notes

Reaction equation

HRID 2389319 reaction equation
[C:1]1([CH:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:31])[N:12]([CH2:14][CH2:15][NH:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:28]=[CH:29][CH:30]=3)[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCO>[C:1]1([CH:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:31])[N:12]([CH2:14][CH2:15][N:16]([CH2:17][C:18]3[CH:19]=[C:20]([CH:28]=[CH:29][CH:30]=3)[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:38])[CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 86637894HCID 86637894, compound

Product 1

HCID 86637893HCID 86637893, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl {3-[({2-[5-(diphenylmethyl)-2-oxopyridin-1(2H)-yl]ethyl}amino)methyl]phenoxy}acetate (90 mg) in EtOH (3 mL) was added sodium triacetoxyborohydride (326 mg) at ambient temperature and the resulting mixture was stirred at ambient temperature for 18 hours. And then the reaction mixture was evaporated in vacuo and partitioned between EtOAc and water. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=20:1) to give ethyl (3-{[{2-[5-(diphenylmethyl)-2-oxopyridin-1(2H)-yl]ethyl}(methyl)amino]methyl}phenoxy)acetate (61.9 mg) as a colorless oil.

Workup

  1. customAnd then the reaction mixture was evaporated in vacuo
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=20:1)

Sources & evidence

ORD record
ord-9793efd9c9b94095ac7b0bec69cb79bd
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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