Methyl iodide → (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazole

Participants

Reaction Steps

130 mg (0.29 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propan-1-ol in 5 mL of THF at 0° C. were treated with 14 mg (0.32 mmol, 1.1 eq) of NaH (55% in oil) portionwise within 30 min. 30 min. 30 μL (0.43 mmol, 1.5 eq) of MeI were added and the reaction mixture was stirred an additional 2 hours, partitioned between EtOAc and a saturated aqueous solution of NH4Cl. The organic phase was washed with brine, dried over Na2SO4, and evaporated. Column chromatography with heptane/EtOAc 1:2 gave 96 mg (72%) of (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazole as a white solid, MS: 479 (MNH4+).

Provenance & Evidence