Aluminium lithium hydride → HCID 67266649, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 27 mg (0.04 mmol) of (RS,SR)-4-[({5-[-benzenesulfonyl-(-7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-amino)-methyl]-benzoic acid methyl ester (example 129.3) in 2 mL THF at 0° C., 40 μl (0.04 mmol, 1 eq) lithium aluminum hydride (1M solution in THF) were added. The reaction mixture was stirred at 0° C. for 1 hour and then at RT for 30 minutes. The reaction was quenched with a saturated NaHCO3 aqueous solution, and the crude product extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel (heptane/EtOAc 2:8) yielded 12 mg (48%) of (RS,SR)-{4-[{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-amino)-methyl]-phenyl}-methanol as a light yellow powder, MS: 581 (MH+).

Provenance & Evidence