6-Methyl-2-pyridinecarboxaldehyde → HCID 23289910, compound

HRID 366415Notes

Reaction equation

HRID 366415 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]1[N:21]=[C:20]([CH:22]=O)[CH:19]=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C.C(O)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:22][C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:15])[N:21]=2)[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23289910HCID 23289910, compoundYield 112.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

In 15 ml of dichloroethane, 315 mg of 4-t-butoxycarbonylaminopiperidine, 320 mg of 6-methyl-2-pyridinecarbaldehyde and 100 mg of acetic acid were dissolved. To the solution 575 mg of sodium triacetoxyborohydride was added at room temperature, followed by an hour's stirring at the same temperature. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and removed of the solvent by reduced pressure distillation. The residue was purified by silica gel column chromatography (chloroform/methanol=100/1 to 50/1), to give 540 mg of the title compound as a white solid.

Workup

  1. waitfollowed by an hour
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customremoved of the solvent by reduced pressure distillation
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/1 to 50/1)

Sources & evidence

ORD record
ord-358804d71bc64f1caa463e9afb698ae2
Source dataset
uspto-grants-2000_10
Patent number
US06130232

Reaction notes

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