Acetic Acid → HCID 57567032, compound

HRID 1819333Notes

Reaction equation

HRID 1819333 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[CH:14]=3)[CH2:10][C:9]2=[O:27])[CH:5]=[CH:6][CH:7]=1.[O:28]1[CH2:32][CH2:31][CH:30]([CH2:33]C=O)[CH2:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>CN(C=O)C>[CH:22]1([O:21][C:15]2[CH:14]=[C:13]([CH:11]3[CH2:12][N:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:33][CH:30]5[CH2:31][CH2:32][O:28][CH2:29]5)[CH:3]=4)[C:9](=[O:27])[CH2:10]3)[CH:18]=[CH:17][C:16]=2[O:19][CH3:20])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 54111073(Oxolan-3-yl)acetaldehydeHCID 68828675HCID 68828675, compound

Product 1

HCID 57567032HCID 57567032, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3-aminophenyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one (8 mg, 0.02 mmol), (tetrahydrofuran-3-yl)-acetaldehyde (0.024 mmol), NaB(OAc)3H (0.2 mmol), and AcOH (0.06 mmol) in DMF (0.5 mL) was stirred for 20 h. After concentration under reduced pressure, the residue was dissolved in EtOAc (3 mL), washed with brine (2×3 mL), and dried over Na2SO4. Concentration and chromatography on silica gel (EtOAc:Hexane=1:1) gave 5.2 mg of the desired product. Yield: 57%.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc (3 mL)
  3. washwashed with brine (2×3 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration and chromatography on silica gel (EtOAc:Hexane=1:1)

Sources & evidence

ORD record
ord-70820f33345c4a93a5aa1d56ddaeed01
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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