Sodium borohydride → 5-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-2-methylthio-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine

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Reaction Steps

The solid from Step 1 is dissolved in MeOH and NaBH4 (210 mg, 5.56 mmol) is added to the solution. The solution is heated at reflux for 4 hr, and then cooled to rt. The solvent is removed in vacuo and the residue is partitioned between water (6 mL) and EtOAc (6 mL). The layers are separated and aqueous layer is extracted with EtOAc (6 ml). The combined extracts are washed with brine (5 ml), dried and evaporated. The residue is purified by PTLC to give the title compound as a light yellow oil. MS (M+1): 351.0; 1H NMR (δ, CDCl3): 3.55-3.65 (m, 6H), 3.40 (s, 2H), 2.87 (t, 2H), 2.65-2.76 (m, 1H), 2.54-2.62 (m, 5H), 2.28 (t, 4H), 1.64-2.06 (m, 6H)

Provenance & Evidence