2-Naphthalenecarboxaldehyde → HCID 43609714, compound

HRID 467955Notes

Reaction equation

HRID 467955 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[CH:18]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[CH2:18][NH:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 62012-NaphthalenecarboxaldehydeHCID 14798Sodium HydroxideHCID 4192234-AminotetrahydropyranHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43609714HCID 43609714, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of tetrahydro-2H-pyran-4-amine (500 mg) in chloroform (5 mL), 2-naphthoaldehyde (772 mg) was added and the resulting mixture was stirred for 30 minutes. Sodium (triacetoxy)borohydride (1.57 g) was added and the resulting mixture was stirred for 4 hours at room temperature. To the reaction mixture, an aqueous solution of 1 M sodium hydroxide was added and after stirring the resulting mixture, the chloroform layer was separated and dried over anhydrous sodium sulfate. After filtering off the desiccant, the solvent was distilled off under reduced pressure and the resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=100:0 to 97:3) to give the titled compound (821 mg).

Workup

  1. stirringthe resulting mixture was stirred for 4 hours at room temperature
  2. stirringafter stirring the resulting mixture
  3. customthe chloroform layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtering off the desiccant
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=100:0 to 97:3)

Sources & evidence

ORD record
ord-dc9d5e83c3804475ac848ff7cf494948
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

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