Hydrochloric Acid → Methyl cis-2-aminocyclobutane-1-carboxylate hydrochloride

HRID 1662081Notes

Reaction equation

HRID 1662081 reaction equation
C(OC([NH:11][C@H:12]1[CH2:15][CH2:14][C@H:13]1[C:16]([O:18][CH3:19])=[O:17])=O)C1C=CC=CC=1.[ClH:20]>[C].[Pd].CO>[ClH:20].[NH2:11][C@H:12]1[CH2:15][CH2:14][C@H:13]1[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11065277HCID 11065277, compound

Product 1

HCID 67429734Methyl cis-2-aminocyclobutane-1-carboxylate hydrochloride

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixture of methyl rel-(1R,2S)-2-{[(benzyloxy)carbonyl]amino}cyclobutanecarboxylate (1.0 g), methanol (20 ml) and 1 M hydrochloric acid (4.0 ml) was added palladium-carbon (4.0 g) at room temperature, followed by stirring at room temperature for 2 hours under a hydrogen atmosphere. The insolubles in the reaction mixture were separated by filtration through Celite and the filtrate was concentrated under reduced pressure. To the residue were added ethyl acetate and acetonitrile, the solid precipitated was separated by filtration, and the filtrate was concentrated to obtain methyl rel-(1R,2S)-2-aminocyclobutanecarboxylate hydrochloride (0.70 g). Methyl rel-(1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithyl}amino)cyclobutanecarboxylate (0.45 g) was obtained by using methyl rel-(1R,2S)-2-aminocyclobutanecarboxylate hydrochloride (0.31 g) in the same method as for Production Process A1.

Workup

  1. customThe insolubles in the reaction mixture were separated by filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue were added ethyl acetate and acetonitrile
  4. customthe solid precipitated
  5. customwas separated by filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ebece6e15c8a4c5386df465b89b0f7ae
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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