Tetrahydro-4H-pyran-4-one → HCID 9802873, compound

HRID 1169428Notes

Reaction equation

HRID 1169428 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH2:10][CH2:11][O:12][C:13]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)=[CH:16][C:14]=3[CH:15]=2)[CH2:4][CH2:3]1.[O:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[CH:18]=[CH:19][C:13]3[O:12][CH2:11][CH2:10][C:9]([CH2:8][N:5]4[CH2:4][CH2:3][CH:2]([NH:1][CH:30]5[CH2:31][CH2:32][O:27][CH2:28][CH2:29]5)[CH2:7][CH2:6]4)=[CH:15][C:14]=3[CH:16]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 22990220HCID 22990220, compound

Product 1

HCID 9802873HCID 9802873, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 4-amino-1-(7-(4-methylphenyl)-2,3-dihydro-1-benzooxepin-4-yl)methylpiperidine (0.4 g) and tetrahydro-4H-pyran-4-one (0.12 g) dissolved in 1,2-dichloroethane (10 ml) was added under ice cooling sodium triacetoxyborohydride (0.34 g), and the resulting mixture was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was evaporated to remove the solvent, was neutralized with a 1 N aqueous solution of sodium hydroxide and was then extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, was then dried with anhydrous magnesium sulfate, and was evaporated under reduced pressure to remove the solvent. The residue was subjected to purification using a silica gel column (methanol/triethylamine/ethyl acetate) to obtain crude crystals. The crude crystals were recrystallized from ethyl acetate/hexane to obtain 1-(7-(4-methylphenyl)-2,3-dihydro-1-benzooxepin-4-yl)methyl-4-((tetrahydropyran-4-yl)amino)piperidine (compound 80) (0.17 g) as colorless crystals.

Workup

  1. additionwas added under ice
  2. customThe reaction mixture was evaporated
  3. customto remove the solvent
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialan aqueous saturated solution of sodium chloride, was then dried with anhydrous magnesium sulfate
  7. customwas evaporated under reduced pressure
  8. customto remove the solvent
  9. customThe residue was subjected to purification
  10. customto obtain crude crystals
  11. customThe crude crystals were recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2ed405ca0ad84ccfb6ea5b22e6829334
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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