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

HRID 2171693Notes

Reaction equation

HRID 2171693 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-4921546db04d464cb2dc38fb6cb8f46e
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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