Tetrahydrofuran → 5-[(2,6-Dimethoxyphenyl)methyl]-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine

HRID 543547Notes

Reaction equation

HRID 543547 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[CH2:17][N:18]1[C:23]2[CH:24]=[CH:25][CH:26]=[N:27][C:22]=2[N:21]2[CH2:28][CH2:29][CH2:30][CH:20]2[C:19]1=O.O1CCCC1>CCOCC>[CH3:16][O:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH3:7])[C:10]=1[CH2:17][N:18]1[C:23]2[CH:24]=[CH:25][CH:26]=[N:27][C:22]=2[N:21]2[CH2:28][CH2:29][CH2:30][CH:20]2[CH2:19]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 133420805-[(2,6-dimethoxyphenyl)methyl]-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 133420815-[(2,6-Dimethoxyphenyl)methyl]-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazineYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (1 g.) was dissolved in 100 ml. of anhydrous diethyl ether. To the stirred solution was added over a period of fifteen minutes a solution of 6a,7,8,9-tetrahydro-5-[(2,6-dimethoxyphenyl)methyl]pyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (1 g., 0.003 mole) in 50 ml. of dry tetrahydrofuran. The reaction mixture was refluxed for eighteen hours and was worked up by adding wet ether, filtering, drying and evaporating in vacuo. The residue (m.p. 110°-112° C.) was dissolved in ethanol and treated with diethyl ether saturated with hydrogen chloride. The separated solid was recrystallized from methanol to afford 0.7 g. (67% yield) of the title compound as the hydrochloride salt, m.p. 211°-213° C.

Workup

  1. temperatureThe reaction mixture was refluxed for eighteen hours
  2. filtrationfiltering
  3. customdrying
  4. customevaporating in vacuo
  5. dissolutionThe residue (m.p. 110°-112° C.) was dissolved in ethanol
  6. additiontreated with diethyl ether saturated with hydrogen chloride
  7. customThe separated solid was recrystallized from methanol
  8. customto afford 0.7 g

Sources & evidence

ORD record
ord-a32edb6a6747409795ca18e0e9f02e1b
Source dataset
uspto-grants-1984_05
Patent number
US04446323

Reaction notes

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