Sodium hydride → HCID 19049372, compound

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Reaction Steps

To a solution of 2-t-butoxycarbonylamino-3,3-diphenylpropan-1-ol (1.0 g, Example 1d) in tetrahydrofuran (5 ml) and dimethylformamide (1 ml) was added sodium hydride (0.11 g, 80% suspension in oil) over 15 minutes. After an additional 10 minutes 3,5-dimethylbenzyI bromide (0.73 g) was added and the solution stirred at room temperature for 3 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. After washing the organic phase with saturated brine and drying (MgSO4), the solvent was removed in vacuo and the residue chromatographed on silica gel in ethyl acetate/hexane (1:10) to give 2-t-butoxycarbonylamino-1-((3,5-dimethylphenyl)methyloxy)-3,3-diphenylpropane 0.38 g. 1H NMR (360 MHz, CDCl3) δ7.3-6.9 (13H, m), 4.7 (1H, bd), 4.6 (1H, bt), 4.43 (1H, d, J=16.7 Hz), 4.3 (2H, m), 3.4 (1H, dd), 3.2 (1H, dd, J=9.4 Hz and 2.82 Hz), 2.3 (6H, s), 1.3 (9H, s). m/z (CI+) 446 (M+H).

Provenance & Evidence