Aluminium lithium hydride → 2-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-2-methyl-propan-1-ol

Participants

Reaction Steps

A solution of 2-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-2-methyl-propionic acid methyl ester (147 mg, 0.31 mmol) in anhydrous THF (5 mL) at 0° C. under nitrogen was treated dropwise with a 1M solution of LiAlH4 in THF (0.47 mL, 0.47 mmol) and the mixture was stirred for 15 minutes then allowed to warm to RT. After 1.5 hours the mixture was cooled to 0° C. and quenched by cautious addition of water. EtOAc was added and the organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The resultant residue was dissolved in DCM (20 mL) and treated with 4N HCl/dioxan (1 mL). The resulting solid was filtered off, washed with ether and dried to give 427 (142 mg, quant.). LCMS: RT=7.54 min, [M+H]+=440. 1H NMR δ (ppm) (DMSO-d6): 10.61 (1 H, s), 8.32 (1 H, d, J=8.21 Hz), 8.07 (1 H, s), 7.22-7.16 (1 H, m), 7.06 (1 H, d, J=1.80 Hz), 5.81-5.72 (1 H, m), 4.55 (1 H, td, J=10.55, 4.79 Hz), 4.38-4.26 (3 H, m), 4.16-3.92 (3H, m), 3.46-3.37 (5H, m), 1.53-1.48 (6 H, m), 1.27-1.14 (6H, m)

Provenance & Evidence