HCID 18348725, compound → HCID 66973470, compound

HRID 1866660Notes

Reaction equation

HRID 1866660 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[NH:14][C:13](=O)[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:10][CH2:11][C:12]([CH3:17])([CH3:16])[CH2:13][NH:14]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 18348725HCID 18348725, compound2×HCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 66973470HCID 66973470, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-(3,4-difluorophenyl)-3,3-dimethylpiperidin-2-one (50.0 mg, 0.209 mmol, prepared according to Intermediate 14, Step A) in THF (1 mL) at 0° C. was added diisobutylaluminum hydride (1.05 mL of a 1 M solution in toluene, 1.05 mmol). The reaction mixture was stirred for 4 days, with additional diisobutylaluminum hydride (1.05 mL of a 1 M solution in toluene, 1.05 mmol) added on the 2nd and 3rd days. The reaction was quenched with saturated potassium sodium tartrate (5 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of MeOH:CH2Cl2—0:100 to 5:95, to give the title compound. MS: m/z=226 (M+1).

Workup

  1. additionadded on the 2nd and 3rd days
  2. customThe reaction was quenched with saturated potassium sodium tartrate (5 mL)
  3. extractionextracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of MeOH

Sources & evidence

ORD record
ord-1871a5f445d444be83063224d227a4f5
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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