Pyrrolidine → 2-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-(pyrrolidin-1-yl)methyl-1,4-cyclohexanediol
Reaction equation
[CH3:1][C:2]([CH3:20])=[CH:3][CH2:4][C@H:5]1[O:7][C@@:6]1([C@@H:9]1[C@:14]2([O:16][CH2:15]2)[CH2:13][CH2:12][C@@H:11]([OH:17])[C@H:10]1[O:18][CH3:19])[CH3:8].[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[O:7]1[CH:5]([CH2:4][CH:3]=[C:2]([CH3:20])[CH3:1])[C:6]1([CH:9]1[CH:10]([O:18][CH3:19])[CH:11]([OH:17])[CH2:12][CH2:13][C:14]1([CH2:15][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[OH:16])[CH3:8]Participants
Conditions
- Temperature
- 50 °C
Procedure
Fumagillol (500 mg) was dissolved in pyrrolidine (1 ml), and the solution was stirred at 50° C. overnight. Excess volume of pyrrolidine was distilled off under reduced pressure to leave 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-(pyrrolidin-1-yl)methyl-1,4-cyclohexanediol as a crude product. This crude product was dissolved in dichloromethane (5 ml), to which was added methyl iodide (1.1 ml), and the mixture was stirred overnight. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography (developing solvent: chloroform-methanol-ammoniacal water=0:1:0.1), followed by pulverizing with ether to obtain 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-(N-methylpyrrolidin-1-ylio)methyl-1,4-cyclohexanediol iodide (446 mg: yield 50%) as colorless powder.
Workup
- distillationExcess volume of pyrrolidine was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-87f287ed2ab34c28af206c570a9f139f
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05180735
Reaction notes
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