Dimethyl Sulfoxide → (S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanal

HRID 1048212Notes

Reaction equation

HRID 1048212 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([C@H:14]1[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]([CH2:40][CH3:41])[C:35](OCC)=[O:36])[C:15]1=[O:42])[CH:12]=[CH2:13].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([C@H:14]1[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]([CH2:40][CH3:41])[CH:35]=[O:36])[C:15]1=[O:42])[CH:12]=[CH2:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 60154134(S)-Ethyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate

Product 1

HCID 58573802(S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanal

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl dichloride (166 μL, 1.87 mmol) in DCM (4.16 mL) at −60° C. was added a solution of DMSO (222 μL, 3.12 mmol) in DCM (4.16 mL) under N2. After about 20 min, a solution of 540 mg (1.25 mmol) of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)piperidin-2-one (Example 9, Step B) in 4.2 mL of DCM was added, and the resulting solution was stirred for 15 min. Triethylamine (872 μL, 6.24 mmol) was then added. After being stirred at −60° C. for 5 min, the reaction was allowed to warm to rt, and 5 mL of water was added. The solution was extracted (2×DCM), washed (sat. aq. NaCl solution), dried (MgSO4) and concentrated under the reduced pressure to give the crude title compound containing 20% starting material (SM).

Workup

  1. stirringAfter being stirred at −60° C. for 5 min
  2. extractionThe solution was extracted (2×DCM)
  3. washwashed (sat. aq. NaCl solution)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under the reduced pressure

Sources & evidence

ORD record
ord-8d9b4227bceb4332b41a5167b7400fe8
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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