Trimethyl orthoformate → 3-Methyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445361

Reaktionsgleichung

Reaktionsgleichung von HRID 445361
CO[C:3](OC)([CH3:29])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)[NH:12][S@@](C(C)(C)C)=O.O1CCOCC1.C(OC)(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.Cl>[CH3:29][CH:3]1[CH2:4][C:5]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:11]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[NH:12]1

Komponenten

7

Edukt 4

HCID 9005Trimethyl orthoformateHCID 312751,4-DioxaneHCID 5049666Sodium triacetoxyborohydrideHCID 59536312(R)-N-((2-(2,2-Dimethoxypropyl)phenyl)(4-(trifluoromethyl)phenyl)-methyl)-2-methylpropane-2-sulfinamide

Produkt 1

HCID 595363073-Methyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

(R)—N-((2-(2,2-Dimethoxypropyl)phenyl)(4-(trifluoromethyl)phenyl)methyl)-2-methylpropane-2-sulfinamide (6.650000 g, 15 mmol) was dissolved in 150 mL of DCE and hydrogen chloride, 4.0 m solution in 1,4-dioxane (11 mL, 44 mmol) was added. Stirring was continued for 20 min and trimethyl orthoformate (8.0 mL, 73 mmol) and sodium triacetoxyborohydride (11 g, 51 mmol) were added. TLC-analysis showed a complex product mixture but LCMS showed the formation of some desired product along with a lot of fully aromatized product. The crude was semi-purified via glass colm chrom and used w/o further clean up in the next steps. MS (ESI, positive ion) m/z: 292.0 (M+1)

Quellen und Nachweise

ORD-Eintrag
ord-88b33395fefa4bd6a02abe47c048b24a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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