Dimethylamine → HCID 67266801, compound

Participants

Reaction Conditions

Reaction Steps

Under argon a flask was charged with 24 mg of (0.03 mmol, 0.05 eq) tris(dibenzylidene-acetone) dipalladium, 16 mg (0.05 mmol, 0.1 eq) of 2(di-tertbutylphosphino)biphenyl and 85 mg (0.88 mmol, 1.7 eq) of sodium tert-butylate, evacuated and backfilled with argon. 300 mg (0.52 mmol) of (RS,SR)-2-(-1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-6-bromo-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester in 15 ml of toluene were added, followed by a solution of 1.95 ml 2M (3.9 mmol, 7.5 eq) of dimethylamine in THF. The solution was heated to 80° C. overnight in a sealed tube. The mixture was diluted with EtOAc and a saturated solution of Na2CO3 was added. The inorganic layer was extracted with EtOAc. The combined organic phases were washed with brine and dried over Na2SO4. Column chromatography yielded 68 mg (24%) of (RS,SR)-2-(-1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-6-dimethylamino-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester as orange oil, MS: 541 (MH+).

Provenance & Evidence