Tetrahydrofuran → HCID 22610872, compound

Participants

Reaction Steps

NaH (480 mg, 80% dispersion, 16 mmol) was added to a solution of 3 (2.10 g, 12.4 mmol) and Bu4NI (228 mg, 0.62 mmol) in THF (50 mL) under N2. After 20 min 2-bromo-1-O-tert-butyldimethylsilylethanol (4.6 g, 19.2 mmol) was added dropwise. After 22 h, the solvent was reduced and the residue partitioned between ether (150 mL) and water (40 mL). The aqueous layer was reextracted with ether (50 mL×2). The organic fractions were combined, washed with brine (40 mL), dried (MgSO4), filtered and the solvent removed. The residue was purified by flash chromatography (EtOAc:hexane, 1:19) to give 5,5-bis(azidomethyl)-1-O-tert-butyldimethylsilyl-3-oxo-hexan-1-ol (5) (2.24 g, 55%) as a colorless oil; IR (film) 2100 (N3) cm−1; 1H NMR (CDCl3, 400 MHz) δ0.05 (s, 6H, Si(CH3)2), 0.88 (s, 9H, SiC(CH3)3), 0.94 (s, 3H, H-6), 3.24 (d, 2H, JH,H′ 11.9 Hz, —CHH′N—×2), 3.26 (s, 2H, H-4), 3.28 (d, 2H, JH,H′ 12.1 Hz, —CHH′N—×2), 3.47-3.50 (m, 2H, H-2), 3.72-3.74 (m, 2H, H-1); 13C NMR (CDCl3, 100 MHz) δ−5.3 (Si(CH3)2), 18.1 (SiC(CH3)), 18.4 (C-6), 25.9 (C(CH3)3), 41.2 (C-5), 55.8 (—CH2N—), 62.6, 73.0, 73.7 (C-1, C-2, C-4); MS m/z (FAB+): 351 (M+Na+, 3), 329 (M+H+, 45).

Provenance & Evidence