6-Methyl-2-pyridinecarboxaldehyde → HCID 10718110, compound

HRID 617375Notes

Reaction equation

HRID 617375 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:24])[C@:9]([C@@H:17]2[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]2)([OH:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.[CH3:25][C:26]1[N:31]=[C:30]([CH:32]=O)[CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[CH3:32][C:30]1[N:31]=[C:26]([CH2:25][N:1]2[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:24])[C@:9]([C@@H:17]3[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]3)([OH:16])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:3][CH2:2]2)[CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 3

HCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10830843HCID 10830843, compound

Product 1

HCID 10718110HCID 10718110, compoundYield 40.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 17 mg of (2R)-N-(piperidin-4-yl)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide in 2 ml of tetrahydrofuran, 3 μl of acetic acid, 12 mg of 6-methylpyridine-2-carbaldehyde and 21 mg of sodium triacetoxyborohydride were added sequentially at room temperature, and stirred overnight at the same temperature. The reaction mixture was diluted with ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, the residue was purified by preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck) chloroform/methanol=10/1) to provide 9 mg of the title compound as a solid substance.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationDistilling the solvent off under reduced pressure
  4. customthe residue was purified by preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck) chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-b8ff128cda67411ba04f1430f1f4861a
Source dataset
uspto-grants-1999_09
Patent number
US05948792

Reaction notes

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