Water → HCID 68001093, compound

HRID 932083Notes

Reaction equation

HRID 932083 reaction equation
[CH2:1]([C@@:4]1([CH3:34])[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]([CH:24]([CH2:31][CH3:32])[CH2:25][C@@H:26]([CH:28]2[CH2:30][CH2:29]2)[OH:27])[C:5]1=[O:33])[CH:2]=[CH2:3].O.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([C@@:4]1([CH3:34])[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@@H:24]([CH2:31][CH3:32])[CH2:25][C:26]([CH:28]2[CH2:29][CH2:30]2)=[O:27])[C:5]1=[O:33])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 67999832HCID 67999832, compound

Product 1

HCID 68001093HCID 68001093, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-cyclopropyl-1-hydroxypentan-3-yl)-3-methylpiperidin-2-one prepared above in Step A (175 mg, 0.350 mmol) and water (9.5 μL, 0.52 mmol) in DCM (3.9 mL) was added Dess-Martin periodinane (222 mg, 0.524 mmol) at rt. After being stirred at rt for 40 min, the reaction was quenched (1 M aq. Na2S2O3), extracted (2×DCM), and washed (2×sat. NaHCO3 and 1×sat. aq. NaCl solution). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification of the residue by chromatography on silica gel (12 g SiO2, 15% and 25% EtOAc/Hex) provided the title compound as a colorless film.

Workup

  1. customthe reaction was quenched (1 M aq. Na2S2O3)
  2. extractionextracted (2×DCM)
  3. washwashed (2×sat. NaHCO3 and 1×sat. aq. NaCl solution)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by chromatography on silica gel (12 g SiO2, 15% and 25% EtOAc/Hex)

Sources & evidence

ORD record
ord-366ddfca439d46df8ca3004623787735
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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