2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile → HCID 10267278, compound

Participants

Reaction Steps

1 N NaOH (100 mL) was added to (6) (6.01 g, 21.4 mmol), followed by extraction with ether (5×50 mL). After a brine wash (50 mL), solvent was removed to give 4.39 g of (6) as the free amine. BOC-ON (5.10 g, 20.7 mmol ) in distilled THF (100 mL) was added to (6) (free amine, 21.1 mmol) in THF (165 mL) at 0° C. over 30 minutes. The reaction was stirred (0° C. to room temperature) for 24 hours and concentrated in vacuo. Cold 1N NaOH (100 mL) was added, followed by extraction with EtOAc (4×100 mL). The organic layer was washed with cold 1 N NaOH (3×80 mL), cold 0.5M citric acid (100 mL) and brine (2×100 mL). Removal of solvent gave 6.38 g (quantitative) of (7), which was used directly in the next step, as a liquid: NMR δ 1.2-1.7 (m+s, 15 H), 2.66-3.23 (m, 4 H), 4.5 (br s, 1 H), 4.67 (s, 2 H), 7.16-7.34 (m, 5 H) . An analytical sample was purified on a silica gel column, eluting with 15% EtOAc/CHCl3. Anal. calcd. for C17H28N2O3 : C, 66.20; H, 9.15; N, 9.08. Found: C, 66.13; H, 9.10; N, 9.05.

Provenance & Evidence