Methanol → (+/-)-2-(1-methyl-2,3-dihydro-1H-inden-1-yl)acetic acid

To a solution of the product from Example 131A (0.47 g, 2.1 mmol) in tetrahydrofuran (6 mL), water (3 mL), and methanol (6 mL) was added 5N NaOH aqueous solution (2.1 mL, 10.8 mmol). After stirring at room temperature for 4 hours, the reaction mixture was concentrated to half the volume, diluted with water (10 mL), washed with methylene chloride (10 mL), acidified to pH˜2 with aqueous 3N HCl solution, and extracted with methylene chloride (3×15 mL). The combined organic extracts were washed with H2O (50 mL), brine (50 mL), dried over MgSO4, filtered, and concentrates under reduced pressure to obtain 0.32 g of the title compound. MS (DCI/NH3) m/z 208 (M+NH4)+

1. concentrationthe reaction mixture was concentrated to half the volume
2. additiondiluted with water (10 mL)
3. washwashed with methylene chloride (10 mL)
4. extractionextracted with methylene chloride (3×15 mL)
5. washThe combined organic extracts were washed with H2O (50 mL), brine (50 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered

ORD record

ord-37ea14ba114f434cbb11e34c6cfe14f8

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609669B2