rac-(1R,3S)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid → rac-methyl (1R,3S)-3-(hydroxymethyl)cyclopentane-1-carboxylate

Temperature

-78 °C

(1S,3R)-3-(methoxycarbonyl)cyclopentanecarboxylic acid (15.9 gm, 92.3 mmol, 1 equi.) was dissolved in anhydrous THF (250 mL) and cooled down to −78° C. under nitrogen atmosphere. To this was added borane dimethyl sulfide complex (2M solution in THF, 1.66 equi., 147.7 mmol, 74 mL) and stirring was maintained for one hour allowing the temperature to raise to 0° C. temperature and stirred at room temperature for another three hours. The mixture was cooled down to −20° C. and quenched with a slow addition of 1M KH2PO4. Reaction was warmed up to room temperature and stirred for further 20 min and extracted with ether. Organic layer was washed with brine and dried over MgSO4, filtered and concentrated to dryness. The residue was purified by silica gel chromatography with (10% to 80% EtOAc in hexanes) to provide 13 g of (1R,3S)-methyl 3-(hydroxymethyl)cyclopentanecarboxylate 99.

1. temperaturewas maintained for one hour
2. temperatureto raise to 0° C. temperature
3. stirringstirred at room temperature for another three hours
4. temperatureThe mixture was cooled down to −20° C.
5. customquenched with a slow addition of 1M KH2PO4
6. customReaction
7. temperaturewas warmed up to room temperature
8. stirringstirred for further 20 min
9. extractionextracted with ether
10. washOrganic layer was washed with brine
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated to dryness
14. customThe residue was purified by silica gel chromatography with (10% to 80% EtOAc in hexanes)

ORD record

ord-effed6a407b84c3eb28093f870aec96b

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859776B2