Methyl iodide → (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester

Participants

Reaction Steps

50 mg (0.1 mmol) (RS,SR)-2-(1-benzenesulfonyl-2-hydroxy-1-methyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester were dissolved in 5 mL dry THF at 0° C. 5 mg (0.11 mmol, 1.1 eq) NaH (55%) were added and the reaction mixture was stirred for 20 minutes. 10 μL (0.15 mmol, 1.5 eq) methyliodide were then added and the reaction was stirred for 1 hour at 0° C. The reaction was quenched with a saturated NaHCO3 solution. The organic phase was washed with brine, dried over Na2SO4, filtered and evaporated to dryness to yield 52 mg (100%) (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester as a white powder.

Provenance & Evidence