Potassium Hydroxide → (6bR,10aS)-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline
Reaction equation
[CH2:1]1[N:10]2[C@H:11]3[CH2:16][CH2:15][N:14](C(OCC)=O)[CH2:13][C@H:12]3[C:8]3[C:9]2=[C:4]([CH:5]=[CH:6][CH:7]=3)[NH:3][CH2:2]1.[OH-].[K+]>C(O)CCC>[CH2:1]1[N:10]2[C@H:11]3[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]3[C:8]3[C:9]2=[C:4]([CH:5]=[CH:6][CH:7]=3)[NH:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 119 °C
Procedure
To ethyl (6bR,10aS)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.10 g, 14.3 mmol) was added n-butanol (18.0 mL) and KOH powder (3.0 g). The reaction was heated at 119° C. in a sealed tube for 18 hr. The solvent was removed under reduced pressure. To the residue was added water (30 mL) extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated to afford the title compound as a pale yellow oil (2.70 g, 78%). MS-ESI: 216 [MH]+
Workup
- customThe solvent was removed under reduced pressure
- additionTo the residue was added water (30 mL)
- extractionextracted with CH2Cl2 (3×50 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1428d693f31c4261b38213835cdf2166
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07183282B2
Reaction notes
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