反应详情

To a suspension of methyl (+/-)-phenylglycinate hydrochloride (4.00 g, 19.8 mmol) in MeOH (50 mL), and HOAc (4 mL) was added 1-phenylmethyl-indole-3-carboxaldehyde (2.85 g, 12.1 mmol). The resulting mixture was allowed to stir at room temperature for 20 minutes; then NaBH3CN (1.98 g, 31.5 mmol) was added in one portion. The suspension was allowed to stir at room temperature for 18 hours, then was concentrated in vacuo to furnish a sticky white semi-solid. The crude reaction mixture was partitioned between 20% aqueous NaOH (0.25 L) and EtOAc (0.25 L); the organic phase was separated, washed with brine (0.25 L), and dried (Na2SO4). Concentration in vacuo afforded the crude product as a pale green oil which was purified by chromatography on a column of silica gel (230-400 mesh, 500 g, 70 mm o.d., EtOAc-hexanes 25:75, 400 mL fractions) using the flash technique. Fractions 8-13 were combined to provide 2.0 g (43%) of the title compound as a white solid. Recrystallization from EtOAc-hexanes provided white needles, m.p. 109°-110° C.

1. stirringto stir at room temperature for 18 hours
2. concentrationwas concentrated in vacuo
3. customto furnish a sticky white semi-solid
4. customThe crude reaction mixture
5. customwas partitioned between 20% aqueous NaOH (0.25 L) and EtOAc (0.25 L)
6. customthe organic phase was separated
7. washwashed with brine (0.25 L)
8. dry with materialdried (Na2SO4)
9. concentrationConcentration in vacuo
10. customafforded the crude product as a pale green oil which
11. customwas purified by chromatography on a column of silica gel (230-400 mesh, 500 g, 70 mm o.d., EtOAc-hexanes 25:75, 400 mL fractions)