Aluminium lithium hydride → HCID 59144134, compound

Participants

Reaction Steps

A solution of LiAlH4 (4.21 mL, 4.212 mmol, 1.0 M solution in THF) was treated dropwise with 7-amino-4-(2-(1-methylpyrrolidin-2-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (0.29 g, 1.053 mmol) in dry THF (5 mL) at 0° C. The resulting mixture was brought to room temperature and stirred overnight. The reaction was carefully quenched with the sequential addition of water (0.16 mL), 2 N NaOH solution (0.16 mL), and water (0.16 mL). The reaction was filtered after stirring for 30 minutes at room temperature and washed with CH2Cl2 (3×10 mL). The combined CH2Cl2 layers were evaporated, and the crude material was purified by column chromatography (5:95 (2M NH3 in MeOH):CH2Cl2) to obtain the title compound (0.23 g, 84%) as a syrup. 1H NMR (DMSO-d6) δ 1.28-1.45 (m, 2H), 1.56-1.65 (m, 2H), 1.75-2.10 (m, 4H), 2.18 (s, 3H), 2.88-2.95 (m, 1H), 3.03-3.10 (m, 4H), 4.08 (t, 2H, J=4.8 Hz), 4.36 (s, 2H), 6.00 (d, 1H, J=2.4 Hz), 6.06 (dd, 1H, J=2.4, 8.5 Hz), 6.43 (d, 1H, J=8.4 Hz); ESI-MS (m/z, %): 262 (MH+, 100), 163 (33), 112 (42).

Provenance & Evidence