4-Pyridinecarboxaldehyde → HCID 11654212, compound

HRID 1786539Notes

Reaction equation

HRID 1786539 reaction equation
[CH3:1][N:2]([CH:19]1[CH2:23][CH2:22][NH:21][CH2:20]1)[C:3](=[O:18])[CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N:24]1[CH:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][N:2]([C@@H:19]1[CH2:23][CH2:22][N:21]([CH2:30][C:27]2[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=2)[CH2:20]1)[C:3](=[O:18])[CH2:4][CH:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 76614146HCID 76614146, compound

Product 1

HCID 11654212HCID 11654212, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-methyl-3,3-diphenyl-N-pyrrolidin-3-yl-propionamide(0.45 g, 1.46 mmol) in CH2Cl2 (10 ml) was added 4-pyridinecarboxaldehyde(0.14 ml, 1.46 mmol), sodium triacetoxyborohydride(0.4 g, 1.89 mmol) and ACOH (0.17 ml, 2.92 mmol). The resulting solution was stirred at room temperature under nitrogen overnight. The reaction mixture was quenched with saturated NaHCO3 (4 ml), and product was extracted with EtOAc (3×30 ml). Drying the EtOAc extract over MgSO4 and removal of solvent under reduced pressure followed by column chromatography using acetone:EtOAc (1:1) gives the desired product in good yield.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 (4 ml), and product
  2. extractionwas extracted with EtOAc (3×30 ml)
  3. dry with materialDrying the EtOAc
  4. extractionextract over MgSO4 and removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-a3bd9ab8933c44248386fa66145baa8d
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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