HCID 178460554, compound → HCID 178460558, compound

Participants

Reaction Steps

A solution of isopropyl (3-t-butyloxyaminocyclopentenyl)methylphosphinate (9) (3.4 g, 10.7 mmol) in methanol (30 cm3) was hydrogenated over platinum oxide (50 mg) at 40 psi for 3 h. The catalyst was removed by filtration through celite and then washed with methanol (3×30 cm3). The solvent was removed in vacuo and the crude product was purified by short column vacuum chromatography on silica gel (15% ethanol/ethyl acetate) to yield the desired cis isomer (10) as a colourless oil (2.1 g, 95%): 1H NMR (300 MHz, CDCl3) δ 1.24 (3H, 2×d, J=6.3 Hz, POCHCH3), 1.32 (3H, d, J=6.3 Hz, POCHCH3), 1.44 (9H, br. s, C(CH3)3), 1.48 and 1.49 (3H, d, J=14.7 and 14.1 Hz, PCH3), 1.58-1.75 (2H, m, C(2)—H, C(4)—H), 2.41-2.72 (5H, m, C(1)—H, C(2)—H′, C(4)—H′, C(5)—H and C(5)—H′), 4.53 (2H, m, POCHCH3 and NH), 4.84 (1H, br. m, C(3)—H),

Provenance & Evidence