Sodium borohydride → ((1S,2R)-1-Furan-2-yl-3-hydroxy-2-methyl-propyl)-carbamic acid tert-butyl ester

Beteiligte Stoffe

Reaktionsschritte

To a solution of 2.2a (2.4 g, 9.48 mmol) in methanol (38 mL) at 0° C. was added NaBH4 (1.8 g, 47.4 mmol, 5.0 equiv). After stirring for 1 hour, the reaction was diluted with EtOAc, washed with saturated aqueous NH4Cl, brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by HPLC purification using AD column: 90/10 heptane/EtOH to afford the desired diastereomer (503.0 mg, 20% yield). 1H NMR (400 MHz, CDCl3) 7.36 (s, 1H), 6.34 (dd, J=3.13, 1.96 Hz, 1H), 6.18 (d, J=3.13 Hz, 1H), 5.13 (br-s, 2H), 3.51 (dd, J=11.74, 5.09 Hz, 2H), 3.33 (t, J=11.15 Hz, 1H), 2.24 (br-s, 2H), 1.47 (s, 9H), 0.73 (d, J=6.65 Hz, 3H).

Herkunft & Nachweise