Nitrogen → HCID 13553301, compound

Participants

Reaction Conditions

Reaction Steps

The compound (1g) (1.0 g, 1.96 mmol) was dissolved in dry THF (5 mL) under N2 and then treated with triethylborane (1 M in THF, 2.9 mL, 2.9 mmol). After aging for 5 minutes, the reaction mixture was cooled to -98° C. (MeOH-liq. N2 bath). Sodium borohydride (85 mg, 2.25 mmol) was added followed by MeOH (2 mL) over 5 minutes. After stirring for an additional 0.5 hours, the reaction mixture was allowed to warm to -60° C. and then was quenched by the careful addition of 30% H2O2 (4 mL) in H2O (10 mL). The mixture was stirred vigourously at ambient temperature for 0.5 hours and then distributed between 1 N HCl (50 mL) and EtOAc (100 mL). The organic layer was washed with H2O (2×50 mL), dried, filtered and evaporated to provide the compound (1h) as a pale yellow gum. 1H NMR shows an 11:1 ratio of erythro vs threo; NMR 0.12 (6 H, s), 0.93 (9 H, s), 1.42-1.61 (2 H, m), 2.32 (6 H, s), 2.34-2.46 (2 H, m), 3.70 (3 H, s), 4.05-4.15 (H, m), 4.3-4.4 (H, m), 4.7-4.85 (2 H, m), 5.29 (H, dd, J=7 and 16 Hz), 6.43 (H, d, J=16 Hz), and 6.50 (H, d, J=16 Hz).

Provenance & Evidence