HCID 67509137, compound → HCID 67509552, compound

HRID 1770757Notes

Reaction equation

HRID 1770757 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:17])[C:11]([CH3:16])([N+:13]([O-])=O)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni].O>[NH2:13][C:11]([CH3:16])([CH3:12])[CH:10]([OH:17])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 67509137HCID 67509137, compound

Product 1

HCID 67509552HCID 67509552, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(benzyloxy)-3-methyl-3-nitrobutan-2-ol (5.2 g, 21.7 mmol) in MeOH (40 ml) was added a slurry of Raney Nickel in H2O (50%, 1 ml). The vessel was pressurized with H2 (450 psi) and the suspension stirred for 24 h. The mixture was filtered through Celite and concentrated in vacuo to give the title compound as a clear liquid (4.0 g, 19 mmol, 89%). 1H NMR (CDCl3, 400 MHz) δ 1.09 (s, 3H), 1.14 (s, 2H), 1.90 (br s, 2H) 3.50-3.54 (m, 2H), 3.61-3.67 (m, 1H), 4.57 (s, 2H), 7.28-7.39 (m, 5H). LRMS (ESI/APCI) m/z 210 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1eda5e8fed604c1b9abc132cf919f2fc
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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