Ethyl Acetate → HCID 23593470, compound

HRID 1242932Notes

Reaction equation

HRID 1242932 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[CH:26][CH:25]=4)=[CH:20][CH:19]=3)=[O:17])[CH:9]=[CH:8][C:7]=2[CH2:6]1)[CH3:3].[BH4-].[Na+].C(OCC)(=O)C>O1CCCC1CO>[CH3:3][N:2]([CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:25]=[CH:26][C:27]([CH2:30][OH:31])=[CH:28][CH:29]=4)=[CH:20][CH:19]=3)=[O:17])[CH:9]=[CH:8][C:7]=2[CH2:6]1)[CH3:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 23593469HCID 23593469, compound

Product 1

HCID 23593470HCID 23593470, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

N-[6-[(N,N-Dimethylamino)methyl]-5,6,7,8-tetrahydro-2-naphthalenyl]-4′-formyl[1,1′-biphenyl]-4-carboxamide (100 mg, 0.242 mmol) was dissolved in tetrahydrofuran-methanol (1:1) solution (2.4 ml), then sodium borohydride (18.3 mg, 0.485 mmol) was added, which was stirred for 2 hours. Ethyl acetate was added to the reaction mixture, which was washed with saturated aqueous sodium chloride solution, dried using anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The residue was pulverized using ether-n-hexane, to give the titled compound (86 mg) as a white powder.

Workup

  1. washwas washed with saturated aqueous sodium chloride solution
  2. customdried
  3. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-1a346374cb874ab9a74ccdf16a43990b
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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