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

HRID 2358018Notes

Reaction equation

HRID 2358018 reaction equation
N[C@H](C1C=CC=CC=1)[C@H](NS(C1C(C)=CC(C)=CC=1C)(=O)=O)C1C=CC=CC=1.C(N(CC)CC)C.[CH2:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][NH:37]1.C(O)=O>C(#N)C.CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[CH2:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][NH:37]1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 8471Triethylamine2×HCID 4225111,2-dihydroisoquinolineHCID 12165385(1R,2R)-N-(2,4,6-trimethylphenylsulfonyl)-1,2-diphenylethane-1,2-diamine

Product 1

HCID 70461,2,3,4-Tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 10908223Dichloro(p-cymene)ruthenium(II) dimerCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  1. additionis added (gas evolution)
  2. concentrationAfter 2 d the mixture is concentrated in vacuo
  3. custompurified by prep

Sources & evidence

ORD record
ord-6e63fd4263d24374941d66bd66204dcf
Source dataset
uspto-grants-2010_07
Patent number
US07763638B2

Reaction notes

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