HCID 117697932, compound → HCID 117698128, compound

HRID 1778534Notes

Reaction equation

HRID 1778534 reaction equation
[CH2:1]([N:8]1[CH:13]2[C:14]([F:17])([F:16])[CH2:15][CH:9]1[CH2:10][CH:11]([OH:18])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[CH2:1]([N:8]1[CH:13]2[C:14]([F:17])([F:16])[CH2:15][CH:9]1[CH2:10][C:11](=[O:18])[CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 117697932HCID 117697932, compound

Product 1

HCID 117698128HCID 117698128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of compound 116g (1.02 g, 4 mmol, 1.0 eq) in DCM (20 mL) was added DMP (3.4 g, 8 mmol, 2.0 eq) slowly at 0° C., then the mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with water, the solid was filtered off, the filtrate was diluted with DCM (100 mL), washed with NaHCO3 (100 mL) three times and brine (100 mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel (EA/PE=1:4) to give 8-benzyl-6,6-difluoro-8-azabicyclo[3.2.1]octan-3-one 116h as a colorless oil. 0.5 g. MS: calc'd (MH+) 252, measured (MH+) 2520.

Workup

  1. additionwas added DMP (3.4 g, 8 mmol, 2.0 eq) slowly at 0° C.
  2. customThe reaction mixture was quenched with water
  3. filtrationthe solid was filtered off
  4. additionthe filtrate was diluted with DCM (100 mL)
  5. washwashed with NaHCO3 (100 mL) three times and brine (100 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel (EA/PE=1:4)

Sources & evidence

ORD record
ord-cdf58f811b8f4a9aa349baad33d1f70e
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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