Tetrabutylammonium Fluoride → HCID 86585983, compound

Participants

Reaction Steps

A stirred, ice cold mixture of the product from Step 10 (0.35 g, 0.78 mmol) and THF (20 ml), under nitrogen is treated, dropwise stirring 3 min, with 1 M tetrabutylammonium fluoride in THF (3.31 ml). It is kept in the ice bath for 5 min and at ambient temperature for 2 h. It is then diluted with EtOAc, washed with water and brine, dried (MgSO4) and concentrated. Chromatography of the residue over silica gel with acetone gave 0.20 g of the titled product: mp 132-136° C.; HRMS (FAB) calcd for C16H19N3O5+H 334.1403, found 334.1418; 1H NMR [300 MHz, (CD3)2SO] δ1.81 (s, 3H), 2.80, 3.01 (m, m, 1H), 3.38 (m, 5H), 3.69 (m, 1H), 4.06 (m, 1H), 4.45 (m, 1H), 4.68 (m, 1H), 4.89, 5.17 (t, t, 1H), 7.26 (m, 1H), 7.38, 7.86 (d, d, 1H), 7.48 (m, 1H), 8.24 (t, 1H), 8.44, 8.95 (s, s, 1H).

Provenance & Evidence