4H-pyran-4-one → N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine

HRID 467952Notes

Reaction equation

HRID 467952 reaction equation
O=[C:2]1[CH:7]=[CH:6][O:5][CH:4]=[CH:3]1.[F:8][C:9]([F:20])([F:19])[O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH2:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl>[F:8][C:9]([F:19])([F:20])[O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH:15][CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 79684H-pyran-4-oneHCID 14798Sodium HydroxideHCID 1452643-(Trifluoromethoxy)benzylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58049381N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amineYield 82.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-oxo-1H-pyran (200 mg) in chloroform (2 mL), 3-trifluoromethoxybenzylamine (380 mg) was added and the resulting mixture was stirred at room temperature for 30 minutes. Sodium (triacetoxy)borohydride (850 mg) was added and the resulting mixture was stirred for an hour. To the reaction mixture, an aqueous solution of 6 M sodium hydroxide was added and extraction was conducted with ethyl acetate. The solvents were distilled off under reduced pressure and the resulting residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=9:1 to 1:9) to give the titled compound (450 mg).

Workup

  1. stirringthe resulting mixture was stirred for an hour
  2. extractionextraction
  3. distillationThe solvents were distilled off under reduced pressure
  4. customthe resulting residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=9:1 to 1:9)

Sources & evidence

ORD record
ord-8db1cfc7e3bc43d68e79f29d8b8cd4c2
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

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