Water → HCID 23157020, compound

HRID 2265149Notes

Reaction equation

HRID 2265149 reaction equation
C(N(S(F)(F)[F:7])CC)C.C(Cl)(Cl)Cl.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1(O)[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:23][CH2:22]1.O>C(OCC)(=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1([F:7])[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 123472(Diethylamino)sulfur trifluorideHCID 23157061Benzyl 4-(2-chlorophenyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 23157020HCID 23157020, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

In a nitrogen atmosphere, 5.26 mL of diethylaminosulfur trifluoride was added to chloroform (160 mL) solution of 5.51 g of benzyl 4-(2-chlorophenyl)-4-hydroxypiperidine-1-carboxylate at −78° C., and stirred for 1 hour at −78° C. Water was added to the reaction liquid, and extracted with chloroform. The chloroform layer was dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was dissolved in 150 mL of acetone/water (2:1) mixture. 15.9 mL of aqueous 0.05 M osmium tetroxide solution and 3.73 g of N-methylmorpholine N-oxide were added thereto, and stirred overnight at room temperature. The reaction liquid was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain 2.11 g of the entitled compound as a colorless oily substance.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe chloroform layer was dried with anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. dissolutionthe residue was dissolved in 150 mL of acetone/water (2:1) mixture
  5. addition15.9 mL of aqueous 0.05 M osmium tetroxide solution and 3.73 g of N-methylmorpholine N-oxide were added
  6. stirringstirred overnight at room temperature
  7. customThe reaction liquid
  8. washwashed with aqueous sodium hydrogencarbonate solution
  9. dry with materialdried with anhydrous sodium sulfate
  10. customThe solvent was evaporated off under reduced pressure
  11. customthe residue was separated
  12. custompurified through silica gel column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-fac1cc0c4cf2407ebd80c37fb059d091
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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