tert-Butyl bromoacetate → HCID 86587571, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 112a (101.6 mg, 0.205 mmol) in 1 mL THF at −78° C., was added 1N LiHMDS in THF (0.431 mL, 0.431 mmol). The mixture was stirred at −78° C. for 10 min, then t-butyl bromoacetate (30.3 μL, 0.205 mmol) was added, dropwise. The mixture was stirred at −78° C. for 5 h, then quenched with sat. NH4Cl. The mixture was diluted with EtOAc and washed with sat. NH4Cl and brine, dried (Na2SO4), and concentrated. The crude product was purified by flash chromatography to afford 110.7 mg (89%) of 112b. 1H NMR (300 MHz, CDCl3) δ9.38 (br s, 1H), 7.63 (br s, 1H), 7.45 (d, J=8.1, 2H), 7.33-7.17 (m, 12H), 7.02 (t, J=7.3, 1H), 5.17-5.11 (m, 3H), 4.84 (br s, 1H), 4.69 (br s, 1H), 3.62-3.51 (m, 1H), 2.84 (d, J=6.9, 2H), 2.79-2.67 (m, 1H), 2.40 (br s, 1H), 1.43 (s, 9H); MS (ESI) 609.2 (M+H+), 631.2 (M+Na+), 607.2 (M−H+).

Provenance & Evidence