Stannous chloride dihydrate → (3S,5R,6S)-3-allyl-1-(5-amino-3-methylpyridin-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one

HRID 932025Notes

Reaction equation

HRID 932025 reaction equation
[CH2:1]([C@@:4]1([CH3:35])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([N+:31]([O-])=O)=[CH:26][N:25]=2)[C:5]1=[O:34])[CH:2]=[CH2:3].O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[CH2:1]([C@@:4]1([CH3:35])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:6]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([NH2:31])=[CH:26][N:25]=2)[C:5]1=[O:34])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 67998434(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-(3-methyl-5-nitropyridin-2-yl)piperidin-2-one

Product 1

HCID 67998447(3S,5R,6S)-3-allyl-1-(5-amino-3-methylpyridin-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-(3-methyl-5-nitropyridin-2-yl)piperidin-2-one (Example 113, Step A) (120 mg, 0.23 mmol) and tin(II) chloride dihydrate (260 mg, 1.1 mmol) were dissolved in 2.3 mL of ethyl acetate. The reaction apparatus was outfitted with a reflux condenser and was stirred at 90° C. for 4 hours. The reaction mixture was cooled to room temperature, quenched with 1M NaOH and extracted (2×EtOAc). The combined organic layers were washed with sat. aq. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography (0 to 90% EtOAc/Hex, gradient elution) provided the title compound as a colorless solid.

Workup

  1. customThe reaction apparatus was outfitted with a reflux condenser
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with 1M NaOH
  4. extractionextracted (2×EtOAc)
  5. washThe combined organic layers were washed with sat. aq. NaCl solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customPurification of the residue
  10. washby flash chromatography (0 to 90% EtOAc/Hex, gradient elution)

Sources & evidence

ORD record
ord-b1915dd6a18b4b21b8a34f4b714befe1
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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