Water → (S)-2-((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)-3-methylbutanal

HRID 1048527Notes

Reaction equation

HRID 1048527 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([C@@:26]1([CH3:53])[CH2:31][C@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=2)[C@@H:29]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)[N:28]([C@@H:46]([CH:49]([CH3:51])[CH3:50])[CH2:47][OH:48])[C:27]1=[O:52])[CH:24]=[CH2:25].O>ClCCl>[CH2:23]([C@@:26]1([CH3:53])[CH2:31][C@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=2)[C@@H:29]([C:39]2[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=2)[N:28]([C@@H:46]([CH:49]([CH3:50])[CH3:51])[CH:47]=[O:48])[C:27]1=[O:52])[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 58573527(3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxy-3-methylbutan-2-yl)-3-methylpiperidin-2-one

Product 1

HCID 58573712(S)-2-((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)-3-methylbutanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (938 mg, 2.212 mmol) was added as a solid to a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxy-3-methylbutan-2-yl)-3-methylpiperidin-2-one (Example 261, Step H, 365.4 mg, 0.794 mmol) in dichloromethane (8 mL) and water (0.04 mL, 2.220 mmol). The resulting suspension was vigorously stirred at ambient temperature for 1.5 h. The reaction was quenched with sodium thiosulfate solution (1M aq, 6 mL). Additional sodium thiosulfate solution (1M aq, 6 mL) was added and stirred until the chalky suspension became a slightly cloudy biphasic mixture. The aqueous phase was separated and back extracted with dichloromethane. The organic layer was washed with sodium thiosulfate solution, saturated aqueous sodium bicarbonate and sat. aq. NaCl solution. After drying over sodium sulfate and concentration, the residue was purified on silica gel, eluting with a gradient of 0 to 30% ethyl acetate in hexanes. Fractions containing the desired product were pooled to give the title compound as a white foam. MS (ESI) m/z=458 [M+H]+.

Workup

  1. customThe reaction was quenched with sodium thiosulfate solution (1M aq, 6 mL)
  2. additionAdditional sodium thiosulfate solution (1M aq, 6 mL) was added
  3. stirringstirred until the chalky suspension
  4. customThe aqueous phase was separated
  5. extractionback extracted with dichloromethane
  6. washThe organic layer was washed with sodium thiosulfate solution, saturated aqueous sodium bicarbonate and sat. aq. NaCl solution
  7. dry with materialAfter drying over sodium sulfate and concentration
  8. customthe residue was purified on silica gel
  9. washeluting with a gradient of 0 to 30% ethyl acetate in hexanes
  10. additionFractions containing the desired product

Sources & evidence

ORD record
ord-59384c11cc7842c9a7318cd108d790bb
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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