Triethylamine → HCID 23157026, compound

HRID 2265142Notes

Reaction equation

HRID 2265142 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C(=O)([O-])O.[Na+].O1[CH2:29][CH2:28]OCC1.[OH2:30]>>[OH:30][CH:7]1[CH:16]([C:15]2[CH:14]=[CH:13][CH:18]=[CH:17][C:28]=2[CH3:29])[CH2:5][CH2:4][N:3]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:6]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 23157026HCID 23157026, compound

Procedure

227 mg of (3RS,4RS)-3-hydroxy-4-o-tolyl-piperidine hydrochloride obtained in Production Example 12 was dissolved in 45 mL of dioxane/water (4:5) mixture, and 405 mg of triethylamine and 269 mg of benzyl chloroformate were added thereto and stirred at room temperature for 4 hours. Aqueous sodium hydrogencarbonate solution was added to the reaction liquid, and extracted with ethyl acetate. The ethyl acetate layer was dried with magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain 253.2 mg of the entitled compound as a pale yellow oily substance.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried with magnesium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe residue was separated
  6. custompurified through silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-2c0c1c74d62e4fa89aa94e697e3dba99
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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