Acetic Acid → HCID 86623631, compound

Temperature

50 °C

To a solution of methyl (R)-(5-cyano-4-methyl-indan-1-yl)acetate (1.00 g, 4.36 mmol, from EXAMPLE 110, Step J) in pyridine (28 mL), acetic acid (15 mL), H2O (15 mL) and NaH2PO2 (3.07 g, 34.9 mmol) Rainey nickel was added (1.0 g) and the mixture was heated to 50° C. After 5 hr, the reaction was concentrated in vacuo and filtered through Celite®. The filtrate was concentrated in vacuo and partitioned between EtOAc (150 mL) and H2O (50 mL). The organic layer was washed with 5.0 N HCl (7×50 mL), sat. NaHCO3 (2×50 mL), brine (1×50 mL) and dried (MgSO4). The mixture was filtered, concentrated in vacuo and purified by flash chromatography (10% EtOAc/hexanes) to give 882 mg of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.76-1.84 (m, 1H), 2.41-2.51 (m, 2H), 2.57 (s, 3H), 2.78 (dd, 1H, J=5.5, 15.6 Hz), 2.81-2.87 (m 1H), 2.93-2.99 (m, 1H), 3.61-3.67 (m, 1H), 3.72 (s, 3H), 7.16 (d, 1H, J=7.8 Hz), 7.63 (d, 1H, 7.8 Hz), 10.2 (s, 1H).

1. concentrationthe reaction was concentrated in vacuo
2. filtrationfiltered through Celite®
3. concentrationThe filtrate was concentrated in vacuo
4. custompartitioned between EtOAc (150 mL) and H2O (50 mL)
5. washThe organic layer was washed with 5.0 N HCl (7×50 mL), sat. NaHCO3 (2×50 mL), brine (1×50 mL)
6. dry with materialdried (MgSO4)
7. filtrationThe mixture was filtered
8. concentrationconcentrated in vacuo
9. custompurified by flash chromatography (10% EtOAc/hexanes)

ORD record

ord-005b7567b70c4558b8813bd37917426a

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07605171B2