Hydrochloric Acid → HCID 58230138, compound

Temperature

-5 °C

A solution of 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (39.5 g) in THF (200 ml) was added dropwise over a period of 45 minutes at −5° C. (ice/methanol bath) to a solution of lithiumdiisopropylamide (2M in THF, 184.3 mL) in THF (300 ml). Stirring was continued for 2.5 hours at 0° C. The reaction mixture was cooled to −5° C. and 2-bromoethyl-methylether (34.6 ml) was added dropwise over a period of 30 minutes. Stirring was continued for 12 hours at RT. The reaction mixture was cooled to 0° C. and aqueous HCl (25%, 300 ml) was added dropwise over a period of 45 minutes to pH 1. Stirring was continued for 2 hours at RT. The reaction mixture was poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a yellow liquid (25.2 g). MS (EI)=288.0 [M+].

1. stirringStirring
2. waitwas continued for 12 hours at RT
3. temperatureThe reaction mixture was cooled to 0° C.
4. stirringStirring
5. waitwas continued for 2 hours at RT
6. extractionextracted two times with ethyl acetate
7. washThe combined organic layers were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. customthe solvent was evaporated
11. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

ORD record

ord-47e8d467df13481c8d7bc3474b767b81

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703807B2