Ethyl 2-(3-formylphenoxy)acetate → HCID 86637894, compound

HRID 2389320Notes

Reaction equation

HRID 2389320 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[CH:10]=[C:9]([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:24].[CH:25]([C:27]1[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=1)[O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:12]1([CH:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:9]2[CH:8]=[CH:7][C:6](=[O:24])[N:5]([CH2:4][CH2:3][NH:2][CH2:25][C:27]3[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=3)[O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:10]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1494377Ethyl 2-(3-formylphenoxy)acetateHCID 5049666Sodium triacetoxyborohydrideHCID 68533638HCID 68533638, compound

Product 1

HCID 86637894HCID 86637894, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-aminoethyl)-5-(diphenylmethyl)pyridin-2(1H)-one hydrochloride (350 mg), ethyl (3-formylphenoxy)acetate (214 mg) and TEA (114 mg) in DCM (10 mL) was added sodium triacetoxyborohydride (326 mg) on ice bath temperature and the resulting mixture was stirred for 4 hours at ambient temperature. And then the reaction mixture was partitioned between DCM and saturated NaHCO3 aqueous solution The organic layer was washed with brine, dried over sodium sulfate and filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=99:1-90:10) to give ethyl {3-[({2-[5-(diphenylmethyl)-2-oxopyridin-1(2H)-yl]ethyl}amino)methyl]phenoxy}acetate (321 mg).

Workup

  1. customAnd then the reaction mixture was partitioned between DCM and saturated NaHCO3 aqueous solution The organic layer
  2. washwas washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=99:1-90:10)

Sources & evidence

ORD record
ord-cf21c12a34884b79ae41a9469078af4a
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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