Reaktion #804553

Reaktionsgleichung

tert-butyl 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

CH3I

H-t-Boc

sodium hydride

→

tert-butyl 5,6-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Lösungsmittel

N,N-dimethylformamide

water

ethyl acetate

—

petroleum ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 50-mL 3-necked round-bottom flask purged
2. 2
   Temperaturmaintained with an inert atmosphere of nitrogen
3. 3
   ExtraktionThe resulting solution was extracted with 3×30 mL of ethyl acetate
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated under vacuum
6. 6
   SonstigeThis resulted in 85 mg (81%) of tert-butyl 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate as a light yellow solid

Vorschrift

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (100 mg, 0.36 mmol, 1.00 equiv) in N,N-dimethylformamide (10 mL) and sodium hydride (12.9 mg, 1.50 equiv). This was followed by the addition of CH3I (254.2 mg, 5.00 equiv). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with 100 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 85 mg (81%) of tert-butyl 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate as a light yellow solid. MS (ESI) m/z 194 ([M+H-t-Boc]+); Rf 0.28 (starting material) and 0.43 (product) in ethyl acetate:petroleum ether=1:3.

Quelle