3-Nitrobenzaldehyde → N-[(3-Nitrophenyl)methyl]oxan-4-amine

Participants

Reaction Steps

NaB(OAc)3H (11.87 mmol, 2.52 g) was added to a mixture of 3-nitrobenzaldehyde Compound 6a (9.89 mmol, 1.49 g) and 4-amino-tetrahydro-pyran Compound 3d (9.89 mmol, 1.00 g) in CH2Cl2 (50 mL) and the resulting suspension was stirred overnight at r.t. The reaction mixture was made basic with a 2N NaOH solution and extracted with CH2Cl2. The organic layer was washed with brine, then separated and dried over MgSO4. The drying agent was filtered and the solvent was removed in vacuo. The product was purified by flash column chromatography (9:1 CH2Cl2:MeOH) to yield (3-nitro-benzyl)-(tetrahydro-pyran-4-yl)-amine Compound 6b as a yellow oil (1.91 g, 82%). (This portion of Example 6 was adapted from Shiroshi, et al., J. Med. Chem., 2000, 43, 2049). MS m/e 237 (M+H, 100%); 1H NMR (300 MHz, CDCl3) δ 1.35-1.53 (m, 4H), 1.82-1.95 (d, 2H), 2.65-2.8 (m, 1H), 3.38 (dt, J=3.2 Hz, J=11.2 Hz, 2H), 3.92-4.05 (m, 4H), 7.45-7.54 (t, 1H), 7.65-7.72 (d, 1H), 8.07-8.15 (d, 1H), 8.22 (s, 1H).

Provenance & Evidence