Acetic Acid → Tert-butyl 3-(piperidin-4-ylmethoxy)azetidine-1-carboxylate

HRID 1021293Notes

Reaction equation

HRID 1021293 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][CH:9]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)=[CH:3][CH:2]=1.C(O)(=O)C>[Pt].CCOC(C)=O>[NH:1]1[CH2:2][CH2:3][CH:4]([CH2:7][O:8][CH:9]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67154567Tert-butyl 3-(pyridin-4-ylmethoxy)azetidine-1-carboxylate

Product 1

HCID 70986787Tert-butyl 3-(piperidin-4-ylmethoxy)azetidine-1-carboxylateYield 97.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-(pyridin-4-ylmethoxy)azetidine-1-carboxylate (4.8 g) was mixed with acetic acid (25 ml) and EtOAc (25 ml), and 10% platinum/carbon was added thereto under argon atmosphere, followed by stirring at room temperature overnight under hydrogen atmosphere of 1 atm. The reaction mixture was filtered using Celite as a filtration adjuvant, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain tert-butyl 3-(piperidin-4-ylmethoxy)azetidine-1-carboxylate (4.8 g).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-525b18e8c5854c1f81b4c33163115ff9
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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