N,N-Dimethylethylenediamine → HCID 67325001, compound

Participants

Reaction Steps

Copper(I) iodide (19 mg, 0.10 mmol) was added to a stirring solution of N,N-dimethyl-1,2-ethanediamine (21 μL, 0.20 mmol) in DMSO (2 mL). The reaction was stirred at RT for 10 minutes. N,N-diisopropylethylamine (130 μL, 0.75 mmol), sodium benzenesulfinate (245 mg, 1.5 mmol) and tert-butyl-8-iodo-1,3a,4,9b-tetrahydrochromeno[3,4-b]pyrrole-3(2H)-carboxylate (P05, enantiomer 1,200 mg, 0.5 mmol) were then added sequentially. The reaction was stirred at 100° C. for 18 h. After cooling to RT, water (24 mL) was added and the resulting suspension was extracted with DCM (3×). The combined organic layers were washed with water (2×) and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting oil was stirred in TFA:DCM (1:1, 2 mL) for 30 min and the solvent was evaporated. This crude product was purified by preparative LC/MS. The resulting material was suspended in DCM, washed with 1N aqueous sodium hydroxide (3×) and water (3×) and the solvent evaporated. The product was converted to the HCl salt by dissolving the free base in a small amount of DCM, adding 1.0 N HCl in diethyl ether and evaporating the solvent to provide 132 mg of 8-(phenylsulfonyl)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-b]pyrrole, Enantiomer 1. MS m/z 316 [M+H]+. 1H-NMR (400 MHz, DMSO-d6): δ 1.91-1.97 (m, 1H), 2.53-2.60 (m, 1H), 2.98-3.02 (m, 1H), 3.19-3.22 (m, 1H), 3.72-3.77 (m, 1H), 4.09 (bs, 1H), 4.24-4.32 (m, 2H), 7.09 (d, J=2.1 Hz, 1H), 7.59-7.74 (m, 4H), 7.94-7.99 (m, 3H), 9.13 (bs, 1H), 9.79 (bs, 1H).

Provenance & Evidence