Tetrahydrofuran → HCID 131720251, compound

Participants

Reaction Conditions

Reaction Steps

BH3 (2.7 mL, 1.0M solution in THF) was added to a solution of 18 (1.12 g, 1.8 mmol) in THF (15 ml) followed by stirring for 3 hr at 23° C. The reaction was quenched by the slow addition of MeOH (0.2 mL). A NaOH solution (6 mL, 3M) was added and the reaction mixture concentrated under reduced pressure to a white solid. The solid was suspended in THF (15 mL) and oxidized by the addition of H2O2 (3 mL, 30% aqueous solution) for 3 hr at 23° C. The solvent was evaporated under reduced pressure and the residue purified by silica gel chromatography (CH2Cl2 /AcOEt, 10:1 then 3:1) to give 0.51 g (44.3%) of the title compound as a white foam. 1H NMR (CDCl3) δ 1.10 (s, 9H, Me3C); 1.18-1.54 (m, 4H); 1.65 (s, 3H, 5-CH3); 2.10-2.40 (m, 3H); 2.18 (t, 1H, J=5.7 Hz, OH); 3.62 (m, 2H, CH2CH2 CH2OH); 3.65 (m, 2H, 5'-H); 4.07 (d, 1H, J=9.8 Hz, 4'-H); 4.71 (s, 2H, OCH2Ph), 5.50 (s, 2H, NCH2O); 6.11 (t, 1H, J=5.1 Hz, 1'-H); 7.26-7.51 (m, 12H, 6-H and aromatic-H); and 7.67-7.70 (m, 4H, aromatic-H).

Provenance & Evidence