Acetic Acid → [1-(Propan-2-yl)piperidin-4-yl]acetic acid

HRID 1360395Notes

Reaction equation

HRID 1360395 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([O:10]C)=[O:9])[CH2:3][CH2:2]1.[CH3:12][C:13]([CH3:15])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.Cl>[CH:13]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1)([CH3:15])[CH3:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 1515259Methyl 4-piperidineacetateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23062749[1-(Propan-2-yl)piperidin-4-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 4-piperidineacetate (0.6 g, 3.82 mmol) was dissolved in methylene chloride (20 mL), acetone (1 mL), acetic acid (0.26 mL) and sodium triacetoxyborohydride (1.21 g, 5.73 mmol) were added, and the mixture was stirred overnight at room temperature. The solvent was evaporated, and work-up according to a conventional method gave a crude product. The obtained crude product was dissolved in 6 N aqueous hydrogen chloride solution, and the mixture was stirred overnight at 80° C. The solvent was evaporated to give the title compound, which was used for the synthesis of A-22.

Workup

  1. customThe solvent was evaporated
  2. customgave a crude product
  3. customThe obtained crude product
  4. stirringthe mixture was stirred overnight at 80° C
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-278b2b9ef82641e8baec3c3413e259c5
Source dataset
uspto-grants-2011_02
Patent number
US07879863B2

Reaction notes

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