Tetrahydrofuran → HCID 55299237, compound
Reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH3:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCC[CH2:17]1>>[CH2:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@H:3]1[CH2:2][NH:1][CH3:17])[CH3:9]Participants
4
Procedure
A solution of the compound obtained in (1) mentioned above in tetrahydrofuran (10 ml) was added dropwise to a suspension of lithium aluminum hydride (590.5 mg) in tetrahydrofuran (20 ml), and the resulting mixture was stirred at room temperature for 0.5 hour, and under reflux by heating for 6 hours. The reaction mixture was cooled to room temperature, then distilled water, 25% aqueous sodium hydroxide and distilled water were added to the reaction mixture in this order under ice cooling, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered thorough Celite, and the filtrate was concentrated under reduced pressure to obtain the title compound (510 mg).
Workup
- temperatureunder reflux
- temperatureby heating for 6 hours
- temperatureThe reaction mixture was cooled to room temperature
- distillationdistilled water, 25% aqueous sodium hydroxide and distilled water
- additionwere added to the reaction mixture in this order under ice cooling
- stirringthe resulting mixture was stirred at room temperature for 1 hour
- filtrationThe reaction mixture was filtered thorough Celite
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0926183c564d41fd8ee657155e534184
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139609B2
Reaction notes
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