Sodium triacetoxyborohydride → HCID 58005166, compound

Participants

Reaction Steps

Hex-5-enal 98 (obtained from hex-5-en-1-ol via a PCC oxidation) (0.95 eq.) was added at RT to a 0.11 M solution of (2S)-1-methoxy-3,3-dimethyl-1-oxobutan-2-aminium chloride (1.0 eq.) and TEA (1.0 eq.) in DCE. Sodium triacetoxyborohydride (1.0 eq.) was added in one portion and the reaction mixture was stirred at RT overnight. The reaction mixture was diluted with DCM/saturated aqueous NaHCO3. The phases were separated; the organic layer was washed with brine, dried (Na2SO4) and filtered though a short path of silica gel (PE:EtOAc=9:1) to afford the title compound 99 as a pale yellow liquid (72%). 1H NMR (300 MHz, CDCl3, 300 K) δ 5.89-5.71 (m, 1H), 5.07-4.88 (m, 2H), 3.71 (s, 3H), 2.88 (s, 1H), 2.62-2.48 (m, 1H), 2.45-2.31 (m, 1H), 2.13-1.98 (m, 2H), 1.67-1.54 (m, 1H), 1.53-1.35 (m, 4H), 0.95 (s, 9H).

Provenance & Evidence