Hydrochloric Acid → Methyl azetidine-3-carboxylate hydrochloride

HRID 1712648Notes

Reaction equation

HRID 1712648 reaction equation
[ClH:1].C([N:15]1[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16]1)(C1C=CC=CC=1)C1C=CC=CC=1>C(OCC)(=O)C.CO.[OH-].[Pd+2].[OH-]>[ClH:1].[NH:15]1[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 2759842Methyl 1-(diphenylmethyl)azetidine-3-carboxylate

Product 1

HCID 21100040Methyl azetidine-3-carboxylate hydrochloride

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4N hydrochloric acid in ethyl acetate (12.7 ml) and 20% palladium hydroxide (3.57 g) were added to a solution of methyl 1-benzhydrylazetidine-3-carboxylate (3.57 g) in methanol (360 ml), followed by stirring under a pressurized hydrogen atmosphere (0.4 MPa) at room temperature for 11 hours. The catalyst was removed by filtration, and washed with methanol and water. The filtrate was concentrated to give a crude product of the target compound as a pale yellow oil, which was used in the next reaction supposing that the reaction proceeded quantitatively and 1.93 g of the product was obtained.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol and water
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d59cdd43a1e14e33a86ea680d469752a
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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