[CH3:1][CH:2]([CH3:12])[C@:3]([C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)([OH:5])[CH3:4].[H][H]>[Pt]=O.CO>[CH3:1][CH:2]([CH3:12])[C@:3]([CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7]1)([OH:5])[CH3:4]Platinum oxide (4.673 g, 20.58 mmol) was placed in a Parr bottle. Methanol (140 mL) was added under an atmosphere of nitrogen followed by (R)-(+)-3-methyl-2-(pyrazin-2-yl)butan-2-ol (17.1 g, 102.9 mmol). The reaction mixture was shaken in a PARR hydrogenator overnight with a hydrogen pressure of 60 psi. Lc/Ms after this time indicate that the reaction was complete. The suspension was filtered through a pad of celite under a nitrogen atmosphere, rinsing with methanol. The crude mixture was concentrated in vacuo. The residue was re-dissolved in dichloromethane, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as viscous light yellow oil (16.6 g, 93%); 1H NMR (CDCl3) 0.82-1.08 (9H, m), 1.81 (1H, m), 2.20-3.17 (10H, m); MS ES(+) 173.0 (M+1).
Loading…
