Tetrahydro-4H-pyran-4-one → HCID 43609892, compound

HRID 1026744Notes

Reaction equation

HRID 1026744 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH2:6][NH2:7].[O:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH2:6][NH:7][CH:15]1[CH2:16][CH2:17][O:12][CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 27249011-(3-Bromo-4-fluorophenyl)methanamine hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43609892HCID 43609892, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (2.52 g) was added to a suspension of 3-bromo-4-fluorobenzylamine hydrochloride (2.79 g) in chloroform (50 mL), and the mixture was stirred at room temperature for 10 min. Tetrahydro-4H-pyran-4-one (2.29 g) was added thereto and the mixture was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (4.85 g) was added thereto, followed by further stirring for 1 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the resulting mixture was then stirred for a while and extracted with chloroform. The organic phase was separated out and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=100:0-90:10) to afford the title compound (2.70 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. stirringby further stirring for 1 hr
  3. stirringthe resulting mixture was then stirred for a while
  4. extractionextracted with chloroform
  5. customThe organic phase was separated out
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=100:0-90:10)

Sources & evidence

ORD record
ord-ca962e1f18aa41f7802b904488075d0c
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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