Water → HCID 69072724, compound

HRID 553950Notes

Reaction equation

HRID 553950 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([N:13]2[C:18](=[O:19])[CH2:17][CH2:16][CH2:15][C@@H:14]2[C:20]([O:22][CH2:23]C)=[O:21])CO)=[CH:6][CH:5]=1.O.C(OCC)(=O)C>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:23][O:22][C@@H:20]([OH:21])[CH:14]3[CH2:15][CH2:16][CH2:17][C:18](=[O:19])[N:13]23)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 67464974HCID 67464974, compound

Product 1

HCID 69072724HCID 69072724, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (70.9 mg) was added to a solution of ethyl (R*)-1-[(R*)-1-(4-fluorophenyl)-2-hydroxyethyl]-6-oxopiperidine-2-carboxylate (290 mg) in methanol (5.0 mL) under ice-cooling, and the reaction solution was stirred for one hour and 40 minutes. Water and ethyl acetate 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 183 mg of the title compound. The property values of the compound are as follows.

Workup

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

Sources & evidence

ORD record
ord-8b9eef9246174df9a568bbdf34bbf0d7
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

Loading…