Hydroxylamine → HCID 16661101, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[(7-tert-butyl-3,4-dihydroisoquinolin-2(1H)-yl)sulfonyl]-1-(tetrahydro-2H-pyran-4-yl)ethanol (431 mg, 1.13 mmol) and Et3N (0.38 ml, 2.71 mmol) in anhydrous THF (10 ml) was cooled at 0° C., then methanesulfonyl chloride (0.105 ml, 1.36 mmol) was added dropwise. The resulting mixture was stirred at 0° C. for 15 min, then at 60° C. for 20 h00. A 50% aqueous solution of NH2OH (1.0 ml, 16.9 mmol)) was added and the resulting mixture was stirred at 60° C. for 2 h30. Then the reaction mixture was washed with brine (5 ml), dried (MgSO4) and the solvent was removed under reduced pressure to give a yellow oil. A mixture of formic acid (3.2 ml) and acetic anhydride (0.8 ml) was stirred at 0° C. for 30 min., then a solution of the previous oil in anhydrous THF (5 ml) was added and the resulting mixture was stirred at 0° C. for 10 min., then at RT for 30 min. The mixture was evaporated under reduced pressure. The residue was taken up with MeOH (10 ml) and heated at 60° C. for 30 min. The reaction mixture was evaporated under reduced pressure, then the residue was taken up with EtOAc (20 ml) and washed with water (2×10 ml), a saturated aqueous solution of NaHCO3 (10 ml) and brine (10 ml). The aqueous layers were extracted with EtOAc (20 ml). The organic layers were combined, dried (MgSO4) and the solvent was removed under reduced pressure to give a yellow oil. After purification by crystallization in EtOAc/Et2O/pentane, the title compound (66) was obtained as a white powder (175 mg, 36%). HPLC, Rt: 4.0 min (purity: 100%). LC/MS, M+(ESI): 425.3, M−(ESI): 422.9.

Provenance & Evidence