Dimethylformamide → HCID 58626994, compound

Temperature

5 °C

Oxalyl chloride (4.14 mL, 47 mmol) was added dropwise to a stirring solution of ((1S,3R)-1-benzyl-3-methyl-cyclopentyl)-acetic acid (10 g, 43 mmol) in dichloromethane under argon at room temperature. The reaction mixture was cooled to 5° C., dimethylformamide (1 mL) was carefully added, and the mixture was allowed to warm to room temperature and stirred for a further 2 hours. The solvent was removed in vacuo and the residue diluted with dichloromethane (60 mL). 1,1-Dimethylethanol (15 mL) was carefully added to the reaction mixture under argon followed by diisopropylethylamine (11.5 mL, 65 mmol). The mixture was stirred for 17 hours and then taken up in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate (2×200 mL), and dried (MgSO4). The solvent was removed under reduced pressure, and the residue was purified by chromatography (silica gel, eluting with a gradient of heptane to 9:1 heptane:ethyl acetate) to give 10.92 g (88%) of ((1S,3R)-1-benzyl-3-methyl-cyclopentyl)-acetic acid tert-butyl ester;

1. temperatureto warm to room temperature
2. customThe solvent was removed in vacuo
3. additionthe residue diluted with dichloromethane (60 mL)
4. addition1,1-Dimethylethanol (15 mL) was carefully added to the reaction mixture under argon
5. stirringThe mixture was stirred for 17 hours
6. washwashed with saturated aqueous sodium hydrogen carbonate (2×200 mL)
7. dry with materialdried (MgSO4)
8. customThe solvent was removed under reduced pressure
9. customthe residue was purified by chromatography (silica gel
10. washeluting with a gradient of heptane to 9:1 heptane

ORD record

ord-d970699412194bbe827e998de4038da4

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06864390B2