Tetrahydrofuran → 2-((2S,3R)-3-(3-chlorophenyl)-2-(4-chlorophenyl)-6-oxopiperidin-1-yl)pentanedial

HRID 932015Notes

Reaction equation

HRID 932015 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12](C3CCC=C3)[C:11](=[O:26])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C[N+]1([O-])CC[O:31][CH2:30]C1.I([O-])(=O)(=O)=O.[Na+].[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>[Os](=O)(=O)(=O)=O.O.CC(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:9][CH2:10][C:11](=[O:26])[N:12]([CH:42]([CH2:41][CH2:45][CH:30]=[O:31])[CH:43]=[O:44])[C@@H:13]2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 58573261(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopent-2-enyl)piperidin-2-one

Product 1

HCID 585737832-((2S,3R)-3-(3-chlorophenyl)-2-(4-chlorophenyl)-6-oxopiperidin-1-yl)pentanedial

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To a solution of 454 mg (1.175 mmol) of (5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopent-2-enyl)piperidin-2-one (Example 104, Step A) in THF (6 mL) was added water dropwise (3.5 mL) and tBuOH (0.2 mL). 4-methylmorpholine 4-oxide (207 mg, 1.763 mmol) was added followed by 4% aq. osmium(VIII) oxide (37.3 μL, 5.88 μmol). The reaction mixture was stirred at room temperature for 18 h. Sodium periodate (704 mg, 3.29 mmol) was added and the cloudy reaction mixture was stirred at room temperature for 90 min. Water (4 mL) was added and the mixture was filtered and washed with EtOAc. The filtrate was diluted with EtOAc and the layers were separated. The combined organic layers were washed with sat. Na2S2O3, sat. aq. NaCl solution, dried over Na2SO4 and concentrated in vacuo to provide the title compound.

Workup

  1. customthe cloudy reaction mixture
  2. stirringwas stirred at room temperature for 90 min
  3. filtrationthe mixture was filtered
  4. washwashed with EtOAc
  5. additionThe filtrate was diluted with EtOAc
  6. customthe layers were separated
  7. washThe combined organic layers were washed with sat. Na2S2O3, sat. aq. NaCl solution
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cec24e5bc9b74be58cfafda9ab48e629
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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