N-(oxolan-3-ylmethyl)ethanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture comprising 4.09g of (tetrahydro-3-furanyl)methyl tosylate, 17 ml of 70% aqueous ethylamine solution and 8.2 ml of 2N aqueous sodium hydroxide solution was stirred at 75° C. for 6 hours. The reaction fluid was concentrated under a reduced pressure to obtain crude N-{(tetrahydro-3-furanyl)methyl}-N-ethylamine. To this were added 2.00 g of 1,1-bis(methylthio)-2-nitroethylene and 20 ml of acetonitrile. The resulting mixture was refluxed for 3 hours. The reaction fluid was concentrated under a reduced pressure, and purified by silica gel column chromatography (eluent:ethyl acetate/hexane=1/2) to obtain 0.81 g of 1-[N-{(tetrahydro-3-furanyl)methyl}-N-ethylamino]-1-methylthio-2nitroethylene. The reaction fluid was concentrated under a reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture comprising 5.5 g of N-{(tetrahydro-3-furanyl)methyl}-N-ethylamine, 3.0 g of S-methyl-N-nitro-N'-methyisothiourea, 30 ml of ethanol and 0.5 g of DMAP was refluxed for 4 hours. Then, the reaction fluid was concentrated under a reduced pressure to obtain an oily matter, which was purified by column chromatography. 1.1 g of 1-{(tetrahydro-3-furanyl)methyl}-1-ethyl-2-nitro-3-methylguanidine were obtained. was refluxed for 4 hours Then, the reaction fluid was concentrated under a reduced pressure to obtain an oily matter, which was purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture comprising 5.5 g of N-{(tetrahydro-3-furanyl)methyl}-N-ethylamine, 3.0 g of S-methyl-N-nitro-N'-methyisothiourea, 30 ml of ethanol and 0.5 g of DMAP was refluxed for 4 hours. Then, the reaction fluid was concentrated under a reduced pressure to obtain an oily matter, which was purified by column chromatography. 1.1 g of 1-{(tetrahydro-3-furanyl)methyl}-1-ethyl-2-nitro-3-methylguanidine were obtained. was refluxed for 4 hours Then, the reaction fluid was concentrated under a reduced pressure to obtain an oily matter, which was purified by column chromatography

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture comprising 4.09g of (tetrahydro-3 -furanyl)methyl tosylate, 17 ml of 70% aqueous ethylamine solution and 8.2 ml of 2 N aqueous sodium hydroxide solution was stirred at 75° C. for 6 hours. The reaction fluid was concentrated under a reduced pressure to obtain crude N-{(tetrahydro-3-furanyl)methyl}-N-ethylamine. To this were added 2.00 g of 1,1-bis(methylthio)-2-nitroethylene and 20 ml of acetonitrile. The resulting mixture was refluxed for 3 hours. The reaction fluid was concentrated under a reduced pressure, and purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/2) to obtain 0.81 g of 1-[N-{(tetrahydro-3-furanyl)methyl}-N-ethylamino]-1-methylthio-2-nitroethylene. The reaction fluid was concentrated under a reduced pressure