Formic Acid → (1S,2S)-(6-fluoro-2-hydroxy-l-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([CH:12]([CH3:14])[CH3:13])[C@:7]([CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])([OH:15])[CH2:6][CH2:5]2.C(O)=O>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([CH:12]([CH3:14])[CH3:13])[C@:7]([CH2:16][C:17]([OH:19])=[O:18])([OH:15])[CH2:6][CH2:5]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
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).
Workup
- temperaturethen heated to 75° C
- filtrationfiltered
- temperatureThe filtrate was slowly cooled to 25° C.
- stirringwith stirring
- temperatureThe resulting suspension was cooled to 0° C.
- stirringstirred for one hour
- filtrationsuction filtered
- washThe precipitate was washed with 15 mL water, air
- customdried at 25° C. for one hour
- customoven dried at 50° C. for 22 hours
Sources & evidence
- ORD record
- ord-9d43e54d803240b1b6138dc608b9deb5
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05811556
Reaction notes
Loading…