Formic Acid → (1S,2S)-(6-fluoro-2-hydroxy-l-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetic acid

A mixture of 3.02 g crude tert-butyl (1S,2S)-(6-fluoro-2-hydroxy-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetate and 8 mL 96% formic acid was stirred at 25° C. for four hours. The solution was diluted with 6 mL water; then heated to 75° C and filtered. The filtrate was slowly cooled to 25° C. with stirring. The resulting suspension was cooled to 0° C., stirred for one hour, and suction filtered. The precipitate was washed with 15 mL water, air dried at 25° C. for one hour, then oven dried at 50° C. for 22 hours to give 1.59 g (1S,2S)-(6-fluoro-2-hydroxy-l-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetic acid as a colorless solid, m.p. 102-103.5° C., [α]D27 = 78.80° (CHCl3).

1. temperaturethen heated to 75° C
2. filtrationfiltered
3. temperatureThe filtrate was slowly cooled to 25° C.
4. stirringwith stirring
5. temperatureThe resulting suspension was cooled to 0° C.
6. stirringstirred for one hour
7. filtrationsuction filtered
8. washThe precipitate was washed with 15 mL water, air
9. customdried at 25° C. for one hour
10. customoven dried at 50° C. for 22 hours

ORD record

ord-9d43e54d803240b1b6138dc608b9deb5

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05811556