3-(benzylamino)-N-methoxy-N-methylcyclobutanecarboxamide → 3-amino-N-methoxy-N-methylcyclobutanecarboxamide

HRID 707352Notes

Reaction equation

HRID 707352 reaction equation
C([NH:8][CH:9]1[CH2:12][CH:11]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])[CH2:10]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]1[CH2:12][CH:11]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])[CH2:10]1

Participants

4

Reactant 1

HCID 866942083-(benzylamino)-N-methoxy-N-methylcyclobutanecarboxamide

Product 1

HCID 450845023-amino-N-methoxy-N-methylcyclobutanecarboxamideYield 95%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(benzylamino)-N-methoxy-N-methylcyclobutanecarboxamide (349 mg, 2.2 mmol) and wet palladium hydroxide on activated carbon (50 wt %, 200 mg) in methanol (30 mL) was stirred under hydrogen (30 psi) at room temperature for 13 hours then the reaction mixture was filtered through CELITE™ H and washed with methanol. The filtrate was concentrated in vacuo to give 3-amino-N-methoxy-N-methylcyclobutanecarboxamide (332 mg, 2.09 mmol, yield 95%).

Workup

  1. filtrationthe reaction mixture was filtered through CELITE™ H
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-84ee059200d14a1abd932bf47428ff73
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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