Sodium Methoxide → 3,4,6,7,8,9-Hexahydro-6,9-methanopyrazino[1,2-a]indol-1(2H)-one

HRID 1919148Notes

Reaction equation

HRID 1919148 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]([C:13](OCC)=[O:14])=[CH:11][C:10]2[CH:9]3[CH2:18][CH:6]([CH2:7][CH2:8]3)[C:5]1=2.C[O-].[Na+]>C(O)C>[CH:6]12[CH2:18][CH:9]([CH2:8][CH2:7]1)[C:10]1[CH:11]=[C:12]3[N:4]([CH2:3][CH2:2][NH:1][C:13]3=[O:14])[C:5]2=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58044168Ethyl 3-(2-Aminoethyl)-3-azatricyclo[5.2.1.02,6]deca-2(6),4-diene-4-carboxylate

Product 1

HCID 580438163,4,6,7,8,9-Hexahydro-6,9-methanopyrazino[1,2-a]indol-1(2H)-oneYield 54.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 3-(2-aminoethyl)-3-azatricyclo[5.2.1.02,6]deca-2(6),4-diene-4-carboxylate (334e) (1.8 g, 7.2 mmol) in ethanol (40 mL) was added sodium meth-oxide (2.5 g, 36 mmol). The mixture was heated at 65° C. for 12 hours. It was then cooled to room temperature. The solvent was evaporated to dryness. The residue was purified by column chromatography eluting with 20:1 methylene chloride/methanol to give 334f as a brown solid (800 mg, 53%). MS: [M+H]+ 203.

Workup

  1. temperatureIt was then cooled to room temperature
  2. customThe solvent was evaporated to dryness
  3. customThe residue was purified by column chromatography
  4. washeluting with 20:1 methylene chloride/methanol

Sources & evidence

ORD record
ord-aab68f628d3b48509f91509dddaddb95
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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