Cesium carbonate → HCID 59300472, compound

Participants

Reaction Steps

To a solution of ethyl [(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (Example 6, 1 g, 4.54 mmol) and (3-Boc-amino)propyl bromide (1.51 g, 6.36 mmol) in DMF (40 mL) was added Cs2CO3 (2.96 g, 9.08 mmol). The mixture was stirred at rt for 18 h, and diluted with a saturated solution of NH4Cl. The mixture was extracted with Et2O and the combined ether extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The product (2.15 g, 94%) was isolated by silica gel column chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD2Cl2) δ 7.05 (d, 1H), 6.77 (s, 1H), 6.69 (dd, 1H), 4.16 (q, 2H), 3.99 (t, 2H), 3.48 (qt, 1H), 3.34-3.25 (m, 2H), 2.95-2.78 (m, 2H), 2.71 (dd, 1H), 2.45-2.33 (m, 2H), 1.95 (qt, 2H), 1.80-1.72 (m, 1H), 1.44 (s, 9H), 1.28 (t, 3H).

Provenance & Evidence