Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → (RS,SR)-2-benzenesulfonyl-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To 100 mg (0.32 mmol) of (RS,SR)-2-benzenesulfonyl-2-(3-oxo-cyclopentyl)-propionic acid methyl ester in glacial acetic acid (3 mL), 63 mg (0.35 mmol, 1.1 eq) of (4-chloro-phenyl)-hydrazine hydrochloride were added and the reaction mixture was heated at 70° C. for about 5 hours. Until completion, the reaction was monitored by HPLC and TLC. An aqueous solution of NaHCO3 was added until pH=7 was reached, and the mixture was extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. A column chromatography on silica gel with heptane/EtOAc 1:1 followed by a trituration with Et2O yielded 45 mg (34%) of (RS,SR)-2-benzenesulfonyl-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester as a light yellow solid, MS: 418 (MH+).

Provenance & Evidence