Dimethyl Sulfoxide → (3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-2-oxopentan-3-yl)piperidin-2-one

HRID 1048406Notes

Reaction equation

HRID 1048406 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([C@@:14]1([CH3:41])[CH2:19][C@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[C@@H:17]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[N:16]([C@@H:34]([CH2:38][CH3:39])[CH:35]([OH:37])[CH3:36])[C:15]1=[O:40])[CH:12]=[CH2:13].C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([C@@:14]1([CH3:41])[CH2:19][C@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[C@@H:17]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)[N:16]([C@@H:34]([CH2:38][CH3:39])[C:35](=[O:37])[CH3:36])[C:15]1=[O:40])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58573239(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((3S)-2-hydroxypentan-3-yl)-3-methylpiperidin-2-one

Product 1

HCID 58573535(3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-2-oxopentan-3-yl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl dichloride (78 μL, 0.87 mmol) in DCM (1.5 mL) at −60° C. was added a solution of DMSO (93 μL, 1.30 mmol) in DCM (1.5 mL) under N2. After being stirred for 2 min, a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((3S)-2-hydroxypentan-3-yl)-3-methylpiperidin-2-one prepared in example 151, Step C (200 mg, 0.434 mmol) in DCM (1.5 mL) was added and the resulting solution was stirred for 15 min. at −60° C. Then, triethylamine (305 μL, 2.17 mmol) was added to the reaction solution. After being stirred at rt for 20 min, the reaction was quenched (water), extracted (2×EtOAc), and washed (2×sat. aq. NaCl solution). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification by combi flash (SiO2, 24 g, 20% and 30% EtOAc/Hexanes) provided the title compound as a colorless foam.

Workup

  1. stirringthe resulting solution was stirred for 15 min. at −60° C
  2. stirringAfter being stirred at rt for 20 min
  3. customthe reaction was quenched (water)
  4. extractionextracted (2×EtOAc)
  5. washwashed (2×sat. aq. NaCl solution)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customPurification by combi flash (SiO2, 24 g, 20% and 30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-43dfcbc8e694464eac8e3680d932cfc3
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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