Sodium borohydride → Rac-8-trifluoromethoxy-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole

To 8-trifluoromethoxy-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole (0.41 g) in THF (2.2 mL) and TFA (4.4 mL) at 0° C. was added portion wise sodium borohydride (0.124 g). The reaction mixture was allowed to warm up to room temperature and stirred for 35 minutes. After such time, the reaction mixture was concentrated in vacuo, and the residue was dissolved in dichloromethane and poured over water. A sodium hydroxide solution (10 M) was the added until reaching pH 13.5. After 15 minutes, the phases were separated. The aqueous phase was extracted with dichloromethane twice. The combined organic layers were then washed with brine, dried with magnesium sulfate, concentrated in vacuo and purified by column chromatography to yield the title compound (0.31 g, 76%).

1. concentrationAfter such time, the reaction mixture was concentrated in vacuo
2. dissolutionthe residue was dissolved in dichloromethane
3. additionpoured over water
4. additionadded
5. waitAfter 15 minutes
6. customthe phases were separated
7. extractionThe aqueous phase was extracted with dichloromethane twice
8. washThe combined organic layers were then washed with brine
9. dry with materialdried with magnesium sulfate
10. concentrationconcentrated in vacuo
11. custompurified by column chromatography

ORD record

ord-5f7d114bb1f243a9a8cb44728396bbc8

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375226B2