Tetrahydrofuran → HCID 53758367, compound

To a stirred solution of ester from Example 59 (1.84 g, 6.13 mmol) in dry THF (15 mL) was added 2M lithium borohydride in THF (5.0 mL, 10.0 mmol) dropwise under nitrogen. The solution was stirred overnight, then quenched by the dropwise addition of methanol (25 mL) and stirred 4 h. The reaction was concentrated, poured into 10% aqueous citric acid (100 mL), and extracted with ethyl acetate (3×100 mL). The combined organic extract was dried over MgSO4 and concentrated. The resulting residue was purified by chromatography (silica gel, ethyl acetate-hexanes, 50:50, 75:25), followed by crystallization from ethyl acetate-hexanes to provide the desired product. (510 mg). m.p=122°-123.5° C.; NMR (300 MHz, DMSO-d6) 1.29 (3H, d, J=7.0 Hz), 2.28 (3H, s), 2.32 (3H, s), 3.08 (2H, m), 3.35 (2H, m), 4.65 (1H, t, J=5.3 Hz), 5.23 (1H, q, J=7.0 Hz), 6.70 (1H, t, J=5.9 Hz), 6.73 (1H, m), 9.03 (1H, s); MS: (M+H)+ =259

1. customquenched by the dropwise addition of methanol (25 mL)
2. stirringstirred 4 h
3. concentrationThe reaction was concentrated
4. additionpoured into 10% aqueous citric acid (100 mL)
5. extractionextracted with ethyl acetate (3×100 mL)
6. extractionThe combined organic extract
7. dry with materialwas dried over MgSO4
8. concentrationconcentrated
9. customThe resulting residue was purified by chromatography (silica gel, ethyl acetate-hexanes, 50:50, 75:25)
10. customfollowed by crystallization from ethyl acetate-hexanes

ORD record

ord-6915f32912c848ef808136fa1ecc6c1a

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05185363