Acetic Acid → HCID 90065720, compound

HRID 522277Notes

Reaction equation

HRID 522277 reaction equation
C([BH3-])#N.[Na+].[NH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH2:6]1.C(O[C:20]1(O[Si](C)(C)C)[CH2:22][CH2:21]1)C.C(O)(=O)C>C1COCC1.CO>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][CH:8]1[CH2:9][CH2:10][N:5]([CH:20]2[CH2:22][CH2:21]2)[CH2:6][CH2:7]1)[CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 2760465Ethyl 2-(piperidin-4-yl)acetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 90065720HCID 90065720, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium cyanoborohydride (2.2 g) was added to a mixture of ethyl 4-piperidine acetate (2.0 g), (1-ethoxycyclopropoxy)trimethylsilane (6.1 g), acetic acid (6.7 mL), a molecular sieve 3A (2.0 g), MeOH (20 mL), and THF (20 mL) at room temperature, and the mixture was stirred at 65° C. for 6 hours. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. After EtOAc was added to the residue, the mixture was stirred, and the insoluble material was separated by filtration. After water was added to the filtrate, potassium carbonate was added to alkalify the mixture. Extraction was performed on the mixture using EtOAc, and the extract was washed with a saturated aqueous NaHCO3 solution and saturated brine. The organic layer was dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=100:0 to 95:5), whereby ethyl(1-cyclopropylpiperidin-4-yl)acetate (2.1 g) was obtained as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionAfter EtOAc was added to the residue
  3. customthe insoluble material was separated by filtration
  4. additionAfter water was added to the filtrate, potassium carbonate
  5. additionwas added
  6. extractionExtraction
  7. washthe extract was washed with a saturated aqueous NaHCO3 solution and saturated brine
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (CHCl3:MeOH=100:0 to 95:5)

Sources & evidence

ORD record
ord-19d8c818363041679f02ed780abfc427
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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