Chloroform → HCID 67464974, compound

HRID 553949Notes

Reaction equation

HRID 553949 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:11]2[C:16](=[O:17])[CH2:15][CH2:14][CH2:13][C@H:12]2[C:18]#N)[CH2:9][OH:10])=[CH:4][CH:3]=1.C(=O)(O)[O-:21].[Na+].C(Cl)(Cl)Cl.Cl.[CH2:30]([OH:32])[CH3:31]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:11]2[C:16](=[O:17])[CH2:15][CH2:14][CH2:13][C@@H:12]2[C:18]([O:32][CH2:30][CH3:31])=[O:21])[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 21887872Ethanol hydrochlorideHCID 69075938HCID 69075938, compound

Product 1

HCID 67464974HCID 67464974, compound

Procedure

A solution of (S*)-1-[(R*)-1-(4-fluorophenyl)-2-hydroxyethyl]-6-oxopiperidine-2-carbonitrile (1.17 g) in saturated hydrochloric acid-ethanol (20 mL) was stirred at room temperature for two days. A saturated sodium bicarbonate solution and chloroform were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 290 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-c52fe9f0421c4575bbcc2dddfb5b2c0b
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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