Lithium hydroxide, monohydrate → 1400689-82-8

Temperature

55 °C

Lithium hydroxide hydrate (407 mg, 9.69 mmol) was added to a solution of (1S,3R)-dimethyl 1,2,2-trimethylcyclopentane-1,3-dicarboxylate (2.213 g, 9.69 mmol) in THF (27.7 ml), water (5.54 ml) and methanol (5.54 ml). The reaction was stirred at 55° C. for 14 hrs. The reaction was cooled to room temperature and concentrated under reduced pressure to yield an oil. The oil was diluted with ethyl acetate and washed with water. The aqueous layer was acidified with 1.0 N HCl, and was extracted with ethyl acetate (3×). The organic extracts were combined, dried with sodium sulfate, filtered and concentrated under reduced pressure, yielding the title compound (1.84 g, 8.59 mmol, 89% yield) as a colorless oil. LC/MS found [M+H]+=215.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.69 (3H, s), 2.84 (1 H, s), 2.52-2.65 (1 H, m), 2.13-2.24 (1 H, m), 1.81-1.90 (1 H, m), 1.53 (1 H, s), 1.27-1.32 (3 H, m), 1.22 (3 H, s), 0.84 (3 H, s).

1. temperatureThe reaction was cooled to room temperature
2. concentrationconcentrated under reduced pressure
3. customto yield an oil
4. washwashed with water
5. extractionwas extracted with ethyl acetate (3×)
6. dry with materialdried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-e88581a07e7b4572afb5381bedf487b8

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921368B2