Formic Acid → 2,2,2-Trifluoro-N-((1R,4R)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Purge a 100 ml round bottom flask containing 0.50 g (1.95 mmol) of (R)-2,2,2-trifluoro-N-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide and 0.062 g (0.098 mmol) RuCl[(R,R)-Tsdpen(p-cymene)] with argon (catalyst prepared using procedure from Org Syn, Vol 82, pg 10-17, note 5). Add 25 ml of dry DMF by syringe and stir. To this solution was added a mixture of 0.43 ml (3.11 mmol) of triethylamine and 0.12 ml (3.11 mmol) of HCOOH. The reaction mixture was stirred at 50° C. overnight. To complete the reaction, additional RuCl[(R,R)-Tsdpen(p-cymene)] (0.062 g), triethylamine (0.43 ml) and HCOOH (0.12 ml) were added and stirring continued at 50° C. for an additional 6-8 hr. The reaction mixture was cooled to room temp, then diluted with 150 ml EtOAc, and washed with 20 ml distilled water. The organic phase was dried over MgSO4 and concentrated in vacuo, and purified by column chromatography (eluting with 1% MeOH in DCM), to give 0.417 g (83%) of the titled compound.

1. customPurge a 100 ml round bottom flask
2. additionTo this solution was added
3. stirringThe reaction mixture was stirred at 50° C. overnight
4. additionwere added
5. stirringstirring
6. washwashed with 20 ml
7. distillationdistilled water
8. dry with materialThe organic phase was dried over MgSO4
9. concentrationconcentrated in vacuo
10. custompurified by column chromatography (eluting with 1% MeOH in DCM)

ORD record

ord-1a275aa1b4804fa39e175361c9850e3b

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915268B2