Water → HCID 13851371, compound

HRID 979166Notes

Reaction equation

HRID 979166 reaction equation
Br[C:2]1[C:7]2[O:8][CH2:9][C@@H:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][C@@H:11]3[C:6]=2[CH:5]=[C:4]([O:17][CH3:18])[CH:3]=1.[CH2:19]([Li])CCC.CI.O>C1COCC1.C(OCC)(=O)C>[CH3:18][O:17][C:4]1[CH:3]=[C:2]([CH3:19])[C:7]2[O:8][CH2:9][C@H:10]3[C@H:11]([CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3)[C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 13851351HCID 13851351, compoundHCID 178418339Butyllithium

Product 1

HCID 13851371HCID 13851371, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.2 g (±)-[4aR*,10bS*]-7-bromo-1,3,4,4a,5,10b-hexahydro-9-methoxy-2-methyl-2H-[1]benzopyrano[4,3-c]pyridine in 25 ml dry THF is added 2.14 ml n-butyllithium (1.98M in hexane). After 30 minutes 0.36 ml CH3I is added and the reaction is warmed to 25° and stirred 1 hour. Water (50 ml) and ethyl acetate (100 ml) is added. The organic phase is washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure, and flash chromatrographed with CH2Cl2 /ammonia saturated methanol (20:1) to afford the title compound; m.p. HCl salt 263° dec.

Workup

  1. temperaturethe reaction is warmed to 25°
  2. washThe organic phase is washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure, and flash

Sources & evidence

ORD record
ord-bdbb1b72eed0455f8f246b301fb5b42f
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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