Fluorine → (R)-8-(1-Isopropyl-piperidin-4-yloxy)-4-methyl-2-((R)-4,4,4-trifluoro-3-hydroxy-butyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Participants

Role	Name	HCID	Charge
Reactant	Fluorine	HCID 24524	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	(3R)-4,4,4-Trifluoro-1,3-butanediol	HCID 2779068	—
Reactant	(3R)-4,4,4-trifluoro-1-(4-methylbenzenesulfonate)-1,3-Butanediol	HCID 11066443	—
Reactant	(R)-8-(1-isopropylpiperidin-4-yloxy)-4-methyl-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one	HCID 16679612	—
Product	(R)-8-(1-Isopropyl-piperidin-4-yloxy)-4-methyl-2-((R)-4,4,4-trifluoro-3-hydroxy-butyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one	HCID 16678930	5%

Reaction Steps

The title compound was synthesized in analogy to example 17, from (R)-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 8), sodium hydride and (R)-toluene-4-sulfonic acid 4,4,4-trifluoro-3-hydroxy-butyl ester (prepared from commercially available (R)-4,4,4-trifluoro-butane-1,3-diol in analogy to M. Tordeux et. al, J. Fluorine Chem. 20, 301 (1982) and U.S. Pat. No. 5,405,967) to give the desired product as a light yellow oil (5%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07579351B2
Source dataset	uspto-grants-2009_08
ORD ID	ord-dc3d5f429f6a4c3d96109c3d61515a2d
Source note	uspto-grants-2009_08