Formic Acid → 1,2,3,4-Tetrahydroisoquinoline

Participants

Role	Name	HCID	Charge
Reactant	Formic Acid	HCID 284	—
Reactant	Triethylamine	HCID 8471	—
Reactant	1,2-dihydroisoquinoline	HCID 422511	—
Reactant	(1R,2R)-N-(2,4,6-trimethylphenylsulfonyl)-1,2-diphenylethane-1,2-diamine	HCID 12165385	—
Catalyst	Dichloro(p-cymene)ruthenium(II) dimer	HCID 10908223	—
Solvent	Acetonitrile	HCID 6342	—
Product	1,2,3,4-Tetrahydroisoquinoline	HCID 7046	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

In a second flask dichloro(p-cymene)ruthenium (II) dimer (0.15 mmol) is added to a solution of N-((1R,2R)-2-amino-1,2-diphenyl-ethyl)-2,4,6-trimethyl-benzene-sulfonamide (0.30 mmol) and triethylamine (0.60 mmol) in acetonitrile (3.3 mL). The mixture is stirred for 1 h at 80° C. A portion of this solution (0.10 mL) is added to the solution of the respective dihydroisoquinoline (described above). An azeotropic mixture of formic acid and triethylamine (5:2, 0.3 mL) is added (gas evolution). After 2 d the mixture is concentrated in vacuo and purified by prep. HPLC to give the respective 1,2,3,4-tetra-hydroisoquinoline.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07763638B2
Source dataset	uspto-grants-2010_07
ORD ID	ord-6e63fd4263d24374941d66bd66204dcf
Source note	uspto-grants-2010_07