Sodium Hydroxide → 1-(2-Phenylethyl)pyrrolidin-2-one

To a solution of HJC-1-48 (4.2 g, 18.6 mmol) in DCM/H2O (20 mL/8 mL) was added (n-Bu)4NBr (0.3 g, 0.9 mmol) and NaOH (3.7 g, 93.0 mmol). The resulting mixture was stirred at 100° C. for 7 h. The mixture was partitioned between EtOAc (200 mL) and H2O (10 mL). The organic layer was separated and washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2) to obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.26-7.30 (m, 2H), 7.18-7.22 (m, 3H), 3.53 (t, 2H, J=7.8 Hz), 3.25 (t, 2H, J=7.2 Hz), 2.84 (t, 2H, J=7.8 Hz), 2.34 (t, 2H, J=7.8 Hz), 1.92-1.97 (m, 2H).

1. customThe mixture was partitioned between EtOAc (200 mL) and H2O (10 mL)
2. customThe organic layer was separated
3. washwashed with brine (20 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give an oil residue
8. customThis residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2)
9. customto obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil

ORD record

ord-104c395a0bdb497a844088336bf10a0a

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328125B2