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

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Reaction Conditions

Reaction Steps

95 mg (0.20 mmol) of (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazole were dissolved in 8 mL of MeOH/THF 1:1, and 5 drops of HCl 12M were added. The temperature was raised to 55° C. and the solution was stirred for 6 hours. By adding 2M NaHCO3 the solution was neutralized to pH=7, and the mixture was extracted with EtOAc. Column chromatography on silica gel with heptane/EtOAc 2:1 yielded 11 mg (13%) of (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-2,3,4,9-tetrahydro-1H-carbazole as a white solid, MS: 418 (MH+).

Provenance & Evidence