HCID 86695090, compound → HCID 89691360, compound

Participants

Reaction Conditions

Reaction Steps

To a 50-mL round-bottom flask, purged and maintained under an inert atmosphere of nitrogen, was added a solution of 26.3 (244 mg, 0.57 mmol, 1.00 equiv) in distilled THF (10 mL) at 0° C. under nitrogen. Then C2H5MgBr (1 M in THF, 2.85 mL, 5.0 equiv) was added dropwise at 0° C. via syringe. The resulting solution was stirred for an additional 2 h at 0° C., quenched with saturated aqueous NH4Cl and extracted with 3×20 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was loaded onto a silica gel column with ethyl acetate/petroleum ether (1:5) and purified to give racemic tert-butyl N-(4-[[(3R)-3-(2-hydroxybutyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]amino]cyclohexyl)carbamate (30.1, 130 mg, 50%) as a colorless oil.

Provenance & Evidence