O-Methylhydroxylamine hydrochloride → HCID 91582857, compound

Participants

Reaction Steps

Add methoxyamine hydrochloride (613 mg, 7.34 mmol) to a solution of (R)-N-[9-(3-fluorobenzyl)-6-formyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 200) (2.40 g, 6.11 mmol) in pyridine (40 mL). Stir the reaction mixture at room temperature for 18 h. Concentrate the reaction in-vacuo and dilute with EtOAc (175 mL). Wash the organics with water (3×75 mL), dry (MgSO4), filter, and concentrate to give the crude product (2.22 g) as a brown foam. Purify the crude product on 40 g silica gel (15-80% EtOAc/hexanes) to give 261 mg (10%) of the title compound as a yellow flaky solid. Re-purify the impure fractions on 40 g silica gel (50-80% (1% (2M NH3/MeOH)/CH2Cl2)/hexanes) and combine the purified materials to give 673 mg (26%) of the title compound as a yellow flaky solid. MS (ES): m/z 422 (M+1), 420 (M−1); HPLC (Method B): Rt=7.98 min (99%).

Provenance & Evidence