Triethyloxonium tetrafluoroborate → Ethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetimidate

HRID 1111611Notes

Reaction equation

HRID 1111611 reaction equation
[CH3:1][C:2]1([CH2:15][C:16]([NH2:18])=[O:17])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.F[B-](F)(F)F.[CH2:24]([O+](CC)CC)[CH3:25]>C(Cl)Cl>[CH2:24]([O:17][C:16](=[NH:18])[CH2:15][C:2]1([CH3:1])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:25]

Participants

4

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 227669211-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetamide

Product 1

HCID 22766953Ethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetimidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetamide (20.0 g., 0.817 mole), described in Example 126, is dissolved in dry methylene chloride (400 ml) and freshly prepared triethyloxonium fluoroborate (17.00 g., 0.894 mole) is added in one portion to the solution. The reaction mixture is stirred at room temperature for 2 hr. The methylene chloride solution is washed with cold 30% aqueous potassium carbonate followed by brine and the dried organic layer is concentrated under reduced pressure. The residue is dissolved in ether (150 ml.). The solution is filtered and crystallization proceeds at room temperature to afford ethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetimidate, m.p. 139.5°-141° C.

Workup

  1. washThe methylene chloride solution is washed with cold 30% aqueous potassium carbonate
  2. concentrationthe dried organic layer is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in ether (150 ml.)
  4. filtrationThe solution is filtered
  5. customcrystallization proceeds at room temperature

Sources & evidence

ORD record
ord-8dc1ec41cef745479b93ad1097cf340c
Source dataset
uspto-grants-1978_10
Patent number
US04118394

Reaction notes

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