Methanol → HCID 86660734, compound

HRID 932168Notes

Reaction equation

HRID 932168 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]([C@H:21]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH2:22][CH3:23])[C:11](=[O:30])[C@:10]([CH2:32][CH:33]([OH:36])CO)([CH3:31])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.I([O-])(=O)(=O)=O.[Na+].CO>O.C1COCC1.[Na+].[Cl-]>[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]([C@H:21]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH2:22][CH3:23])[C:11](=[O:30])[C@:10]([CH2:32][CH:33]=[O:36])([CH3:31])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 23667635Sodium periodateHCID 67998290HCID 67998290, compound

Product 1

HCID 86660734HCID 86660734, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(2,3-dihydroxypropyl)-3-methyl-1-((1S)-1-(tetrahydro-2H-pyran-2-yl)propyl)piperidin-2-one (3 mg, 5.61 μmol; Example 224, Step D) in water (20.0 μL) and THF (40.0 μL) was treated with sodium periodate (3.60 mg, 0.02 mmol). After a precipitate formed, methanol (40 μL) was added to form an emulsion which was stirred at ambient temperature for 1 hour. The reaction was diluted with sat. aq. NaCl solution and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the filtrate was concentrated to provide a mixture of two diastereomers which was used in the next step. Mass Spectrum (ESI) m/z=502.1 (M+1)

Workup

  1. customAfter a precipitate formed
  2. customto form an emulsion which
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto provide
  8. additiona mixture of two diastereomers which

Sources & evidence

ORD record
ord-a58f7aef8a204aeb812ab492dd77c414
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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