Acetic Acid → (1r)-1-(4-Piperidinyl)ethanol acetic acid salt

HRID 423656Notes

Reaction equation

HRID 423656 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C@H:7]([OH:9])[CH3:8])=[CH:3][CH:2]=1.[CH3:10][C:11]([OH:13])=[O:12]>CO.O=[Pt]=O>[C:11]([OH:13])(=[O:12])[CH3:10].[NH:1]1[CH2:6][CH2:5][CH:4]([C@H:7]([OH:9])[CH3:8])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 11804747(1R)-1-(pyridin-4-yl)ethan-1-ol

Product 1

HCID 66673151(1r)-1-(4-Piperidinyl)ethanol acetic acid saltYield 79.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

(1R)-1-(4-pyridinyl)ethanol (61 g, 495 mmol, 96% ee) was dissolved in MeOH (1.5 L). The mixture was flushed with nitrogen and AcOH (40 mL, 0.7 mol) and PtO2 (15 g) were added. The mixture was stirred overnight under an atmosphere of hydrogen. The catalyst was removed by filtration and washed with MeOH (2×100 mL) and the filtrate was concentrated. The solid residue was mixed with EtOAc (500 mL) and stirred overnight. The resulting solid was collected by filtration, washed with EtOAc (3×100 mL) and dried under vacuum overnight to yield (1R)-1-(4-piperidinyl)ethanol acetic acid salt (74.5 g, 79% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): 3.30 (m, 1H), 3.03 (m, 2H), 2.55-2.50 (m, 2H), 1.76-1.69 (m, 1H), 1.69 (s, 3H), 1.51-1.44 (m, 1H), 1.27-1.16 (m, 3H), 0.96 (d, 3H, J=6.3 Hz).

Workup

  1. additionwere added
  2. customThe catalyst was removed by filtration
  3. washwashed with MeOH (2×100 mL)
  4. concentrationthe filtrate was concentrated
  5. additionThe solid residue was mixed with EtOAc (500 mL)
  6. stirringstirred overnight
  7. filtrationThe resulting solid was collected by filtration
  8. washwashed with EtOAc (3×100 mL)
  9. customdried under vacuum overnight

Sources & evidence

ORD record
ord-eb2aff83593c467f9fb5fff1380f184a
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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