Ammonium Hydroxide → HCID 56776968, compound

HRID 1749437Notes

Reaction equation

HRID 1749437 reaction equation
O[N:2]=[C:3]1[CH2:6][CH:5]([C:7]([O:9][CH3:10])=[O:8])[C:4]1([CH3:12])[CH3:11].[OH-].[NH4+].[H][H]>CO.[Ni]>[NH2:2][CH:3]1[CH2:6][CH:5]([C:7]([O:9][CH3:10])=[O:8])[C:4]1([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 131733580HCID 131733580, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 56776968HCID 56776968, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(hydroxyimino)-2,2-dimethylcyclobutanecarboxylate (1.0 equiv.) in MeOH (0.4 M) was added ammonium hydroxide (0.2 M) and Raney nickel (20 wt percent). The mixture was stirred at 50° C. under 50 psi hydrogen atmospheres for about 6 h. After completion of the reaction, the mixture was filtered through celite. The filtrate was concentrated in vacuo to give the crude title compound methyl 3-amino-2,2-dimethylcyclobutanecarboxylate (82.3% yield) as green liquid. The product was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 3.56 (s, 3H), 2.50 (s, 0.4H), 2.14 (s, 0.24H), 1.94 (s, 0.35H), 1.71 (s, 0.73H), 1.05 (s, 2.0H), 0.76 (s, 2H).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3d040ea419bd42109e62f670b087a560
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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