Methanol → 1392803-57-4

HRID 1749475Notes

Reaction equation

HRID 1749475 reaction equation
O[N:2]=[C:3]1[CH2:6][CH:5]([NH:7][C:8](=NO)[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:4]1([CH3:17])[CH3:16].C[OH:19]>N.[Ni]>[NH2:2][CH:3]1[CH2:6][CH:5]([NH:7][C:8](=[O:19])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:4]1([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 887MethanolHCID 176533515HCID 176533515, compound

Product 1

HCID 1127028651392803-57-4Yield 76%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

To a solution of tert-butyl (3-(hydroxyimino)-2,2-dimethylcyclobutyl)carbamate oxime (730 mg, crude) in MeOH and ammonia (12.5 mL and 2.5 mL) was added Raney-Ni (430 mg, crude). The reaction mixture was stirred at room temperature under hydrogen atmosphere overnight. The reaction was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (2-5% MeOH in DCM) to afford the title compound (490 mg, 2.29 mmol, 76% yield two steps). MS (ESI) m/z 215.2 [M+H]+.

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (2-5% MeOH in DCM)

Sources & evidence

ORD record
ord-42605c2fee0c4ea8ad3033eaaf989c01
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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