Sodium Thiosulfate → HCID 86638699, compound

HRID 1691700Notes

Reaction equation

HRID 1691700 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[C@H:13]([CH2:14][OH:15])[CH2:12][CH2:11][N:10]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[C@H:13]([CH:14]=[O:15])[CH2:12][CH2:11][N:10]([C:16](=[O:21])[C:17]([F:18])([F:19])[F:20])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 87198708HCID 87198708, compound

Product 1

HCID 86638699HCID 86638699, compoundYield 122.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.50 g of rel-[(3R,4R)-3-(3-fluorophenyl)-1-(trifluoroacetyl)piperidin-4-yl]methanol in 15 mL of dichloromethane was added 2.29 of Dess-Martin Periodinane at room temperature, followed by stirring for 1.5 hours. To the reaction mixture were added a saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was washed with water and saturated brine in this order, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 1.83 g of crude rel-(3R,4R)-3-(3-fluorophenyl)-1-(trifluoroacetyl)piperidine-4-carbaldehyde as an orange oily compound.

Workup

  1. extractiona saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform
  2. washThe organic layer was washed with water and saturated brine in this order
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-27761ba9e708465da81eefbfbbb13264
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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