Methanol → 219496-46-5

Temperature

-78 °C

To a solution of (1S,3R)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid (5.1 g, 25.5 mmol) in methanol (63.7 ml) at −78° C. was added thionyl chloride (2.045 ml, 28.0 mmol). After stirring at −78° C. for 30 minutes, the reaction was allowed to warm to room temperature. Stirring was continued for 14 hrs. The reaction mixture was concentrated under reduced pressure, yielding a yellow oil. The oil was taken into water. The solution was adjusted to pH 12 with 1.0 N NaOH and was washed with ethyl acetate. The basic aqueous layer was acidified with 1.0 N HCl, and was extracted with ethyl acetate (3×, 100 ml). The ethyl acetate extracts were combined, dried with sodium sulfate, filtered, and concentrated under reduced pressure to afford (1S,3R)-3-(methoxycarbonyl)-1,2,2-trimethylcyclopentanecarboxylic acid (5.35 g, 24.97 mmol, 98% yield) as a colorless oil. ESI-MS m/z 237.1 ([M+H]+).

1. temperatureto warm to room temperature
2. stirringStirring
3. waitwas continued for 14 hrs
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. customyielding a yellow oil
6. washwas washed with ethyl acetate
7. extractionwas extracted with ethyl acetate (3×, 100 ml)
8. dry with materialdried with sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-a725d7288b3142a383e3eeaa7c96d587

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921368B2