Water → HCID 59837531, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-({4-[4-(3-azetidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}carbonyl)morpholine (120 mg, 0.31 mmol) in THF (1 mL) at 0° C. was added dropwise a solution of LiAlH4 (1.0M solution in Et2O, 1.00 mL, 1.00 mmol). The reaction mixture was stirred at 0° C. for 20 mins then heated at reflux for 3 hours. The reaction was then cooled to 0° C., water (0.10 ml) was added dropwise followed by sodium hydroxide (2.0M, 0.10 ml) and water (0.30 ml). The mixture was filtered through a short pad of celite, eluting with 1% methanol in dichloromethane (15 ml) and the organic washings concentrated in vacuo. The crude compound was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:ammonia, 97:3:0.3 to 94:6:0.6, to give the title compound as a clear oil (25 mg, 22%). 1H NMR (400 MHz, CDCl3) δ 1.78-1.90 (m, 8H), 2.08 (m, 2H), 2.13 (m, 4H), 2.38 (s, 2H), 2.59 (t, 2H), 3.20 (t, 2H), 3.51 (m, 6H), 3.76 (m, 2H), 4.00 (t, 2H), 6.82 (d, 2H), 7.21 (d, 2H). LRMS APCI+ m/z 375 [MH]+.

Provenance & Evidence