Acetic Acid → HCID 86592537, compound

HRID 1374448Notes

Reaction equation

HRID 1374448 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@H:8]([CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:9][C:10]([O:12]CC)=O)=[O:6])[CH:2]=[CH2:3].[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH:25]=[CH2:26].[H-].[Na+].Cl.C(O)(=O)C.C([BH3-])#N.[Na+]>C1(C)C=CC=CC=1>[Si:17]([O:16][CH2:15][C@H:8]1[N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH2:26][CH:25]([C:24]([O:28][CH2:29][CH3:30])=[O:27])[CH:10]([OH:12])[CH2:9]1)([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:18])[CH3:19]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 24758Sodium hydrideHCID 5003444Sodium cyanoborohydrideHCID 86592538HCID 86592538, compound

Product 1

HCID 86592537HCID 86592537, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl (3S)-3-{[(allyloxy)carbonyl]amino}-4-{[tert-butyl(dimethyl)silyl]oxy}butanoate (1.25 g, 3.6 mmol) and ethyl acrylate (0.39 ml, 3.6 mmol) in toluene (10 ml) was added at 40° C. sodium hydride (60% suspension in oil, 145 mg, 3.6 mmol). The mixture was stirred at 60° C. for 1 hour and then poured into diluted hydrochloric acid. The solution was extracted three times with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed in vacuo. The residue was dissolved in methanol(25 ml) and to the solution were added acetic acid (0.25 ml, 4.4 mmol) and sodium cyanoborohydride (0.27 g, 4.3 mmol). The mixture was stirred at room temperature for 30 minutes. The solvent was removed in vacuo and the residue was purified with silica gel chromatography to give 1-allyl 3-ethyl (6S)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-hydroxy-1,3-piperidinedicarboxylate (0.48 g, 33%).

Workup

  1. extractionThe solution was extracted three times with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in methanol(25 ml) and to the solution
  6. stirringThe mixture was stirred at room temperature for 30 minutes
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-043d1ec531344c2aa1d764ff2a56067a
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

Loading…