Hydrochloric Acid → tert-butyl 4-(azetidin-3-yl)piperidine-1-carboxylate

HRID 1021300Notes

Reaction equation

HRID 1021300 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)C=CC=CC=1.Cl.[OH-].[Na+]>[OH-].[C+4].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-].CO>[NH:8]1[CH2:11][CH:10]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]2)[CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86686243HCID 86686243, compound

Product 1

HCID 73553659tert-butyl 4-(azetidin-3-yl)piperidine-1-carboxylateYield 97.9%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 4-[1-(diphenylmethyl)azetidin-3-yl]piperidine-1-carboxylate (1.9 g) was mixed with MeOH (50 ml), and 1 M hydrochloric acid (5.1 ml) and 20% palladium carbon hydroxide (600 mg) were added thereto, followed by stirring at room temperature for 4 hours under hydrogen atmosphere of 3 atm. After returning to normal pressure under argon atmosphere, a 1 M aqueous NaOH solution (1 ml) was added thereto. The reaction mixture was filtered using Celite as a filtration adjuvant, and the filtrate was concentrated under reduced pressure. CHCl3 and a 1 M aqueous NaOH solution were added to the obtained residue, and the organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (CHCl3/MeOH) to obtain tert-butyl 4-(azetidin-3-yl)piperidine-1-carboxylate (1.1 g).

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionCHCl3 and a 1 M aqueous NaOH solution were added to the obtained residue
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by basic silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-1ded438fa4b64e3993d5c23cd53533e9
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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