1,6-Dioxaspiro[2.5]octane → 4-{[(2R,5S)-4-benzyl-2,5-dimethylpiperazin-1-yl]methyl}tetrahydro-2H-pyran-4-ol
Reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2]1.[CH2:9]([N:16]1[CH2:21][C@@H:20]([CH3:22])[NH:19][CH2:18][C@@H:17]1[CH3:23])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[CH2:9]([N:16]1[C@@H:17]([CH3:23])[CH2:18][N:19]([CH2:2][C:3]2([OH:1])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[C@H:20]([CH3:22])[CH2:21]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a microwave vial was added 1,6-dioxaspiro[2.5]octane (259 mg, 2.3 mmol), (2S,5R)-1-benzyl-2,5-dimethylpiperazine (464 mg, 2.3 mmol) and 5 mL of MeOH. The vial was heated to 150° C. for 2 h in the microwave. The crude reaction was concentrated to provide intermediate H1(ii) (723 mg, 100%) 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.92 (d, J=6.22 Hz, 3H), 1.13 (d, J=5.84 Hz, 3H), 1.35-1.45 (m, 1H), 1.46-1.68 (m, 4H), 1.83 (dd, J=11.30, 9.80 Hz, 1H), 2.12 (d, J=13.94 Hz, 1H), 2.36-2.53 (m, 3H), 2.60-2.69 (m, 2H), 2.85 (d, J=9.04 Hz, 1H), 3.08 (d, J=13.38 Hz, 1H), 3.71-3.82 (m, 4H), 4.04 (d, J=13.38 Hz, 1H), 7.10-7.47 (m, 5H). Mass Spectrum: Calcd for C19H30N2O2 (M+H): 318. Found: 318.