tert-butyl N-(2-oxoethyl)carbamate → tert-butyl N-(2-hydroxybut-3-en-1-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a suspension of dried, powdered 4 A molecular sieves (18 g) and PDC (45 mg, 120 mmol) in 150 mL CH2Cl2 was added a solution of 2-(BOC-amino)ethanol (4.83 g, 30 mmol) in CH2Cl2. The mixture was allowed to stir at ambient temperature for 1.5 hour, then diluted with ether (200 mL) and filtered through a silica gel pad, rinsing throughly with ether. The filtrate was concentrated to afford a clear pale yellow oil (3.46 g, 72%). The aldehyde was used immediately for the next reaction without purification. To a cooled solution of the freshly prepared BOC-Glycinal (410 mg, 2.6 mmol) in 8 mL THF was slowly added 1.0M vinyl magnesium bromide in THF (18 mL) via syringe. The reaction mixture was allowed to stir for 1 hour with warming to -10° C. The reaction was quenched with saturated aqueous ammonium chloride (20 mL) and was extracted with chloroform (×4). The extracts were dried and concentrated. The crude oil was purified by flash chromatography on silica gel, eluting with EtOAc/hexane (1/5~1/1, v/v) to give the title compound as a clear pale yellow oil (380 mg, 78% yield). MS(DCI) m/e 205(M+NH4)+. 1H NMR(CDCl3, 300 MHZ) δ1.45 (s, 9H), 2.54 (br s, 1H), 3.10 (dt, 1H), 3.30-3.43 (m, 1H), 4.24 (br s, 1H), 4.92 (br s, 1 H), 5.21 (d, 1H), 5.35 (d, 1H), 5.86 (ddd, 1H). Anal calc for C9H17NO3 : C, 57.72; H, 9.17; N, 7.48. Found: C, 57.85; H, 9.19; N, 7.42.

Provenance & Evidence