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

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).

1. extractionextracted with CH2Cl2
2. washThe organic layer was washed with brine
3. customseparated
4. dry with materialdried over MgSO4
5. filtrationThe drying agent was filtered
6. customthe solvent was removed in vacuo
7. customThe product was purified by flash column chromatography (9:1 CH2Cl2:MeOH)

ORD record

ord-51ece4a3b434405484e4bb272ec5d9cb

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07799824B2