1,3-Dibromobutane → HCID 21931679, compound

Participants

Reaction Steps

To diethylamine (4.32 g, 59.0 mmol) in 22 mL of THF at 0° C. was added nBuLi (2.5 M in hexanes; 50.6 mmol, 20.2 mL). After 15 minutes the solution was added via cannula to a −50° C. solution of 1-(tert-Butyl-dimethyl-silanyl)-4-phenyl-azetidin-2-one (11.0 g, 42.2 mmol) in 110 mL of THF. After stirring for 20 minutes, 1,3-dibromobutane was added and the solution was stirred for 1 hour. Saturated aqueous NH4Cl was added and the mixture was warmed to room temperature and extracted once with ether. The extract was dried with MgSO4, concentrated and chromatographed (9:1 hexanes/EtOAc) to give 11.4 g (68%) of the title compound as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ comp, 10H), 4.21 (d, J=2.5 Hz, 1H), 4.16 (d, J=2.5 Hz, 1H), 4.08 (m, 1H), 3.02 (m, 1H), 1.80–2.10 (comp, 4H), 1.67 (d, J=6.6 Hz, 3H), 0.90 (s, 9H), 0.18 (s, 3H), −0.22 (s, 3H); Mass spectrum m/e calcd for M+H=396.2. Found 396.0 (base), 316.

Provenance & Evidence