diethyl 2-(3-cyanopropyl)propanedioate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-methyl-3-nitro-pyridine (20 g) was reacted with 2-(3-cyanopropyl)malonic acid diethyl ester under conditions analogous to those in Example 1(a). The reaction mixture was partitioned between water and chloroform, the chloroform extract was dried, treated with charcoal and filtered through a silica bed and then evaporated to dryness to give 2-[4-cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine (18.3 g) as a yellow oil. N.M.R. (CDCl3) assignment, δ(p.p.m.), multiplicity; CO2CH2CH3 ×2, 1.2, t; --CH2CH2CH2CN, 1.3-2.0, m; --CH2CN, 2.37, m; 5-methylpyridyl, 2.49, s; CO2CH2CH3 ×2, 4.19, q; 4-pyridyl proton 8.17, m; 6-pyridyl proton, 8.57, m; The reaction mixture was partitioned between water and chloroform the chloroform extract was dried treated with charcoal filtered through a silica bed evaporated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-methyl-3-nitro-pyridine (20 g) was reacted with 2-(3-cyanopropyl)malonic acid diethyl ester under conditions analogous to those in Example 1(a). The reaction mixture was partitioned between water and chloroform, the chloroform extract was dried, treated with charcoal and filtered through a silica bed and then evaporated to a dryness to give 2-[4-cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine (18.3 g) as a yellow oil. The reaction mixture was partitioned between water and chloroform the chloroform extract was dried treated with charcoal filtered through a silica bed evaporated to a dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-methyl-3-nitro-pyridine (20 g) was reacted with 2-(3-cyanopropyl)malonic acid diethyl ester under conditions analogous to those in Example 1(a). The reaction mixture was partitioned between water and chloroform, the chloroform extract was dried, treated with charcoal and filtered through a silica bed and then evaporated to dryness to give 2-[4-cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine (18.3 g) as a yellow oil. N.M.R. (CDCl3) assignment, δ(p.p.m.), multiplicity; CO2CH2CH3 ×2, 1.2, t; --CH2CH2CH2CN, 1.3-2.0, m; --CH2CN, 2.37, m; 5-methylpyridyl, 2.49, s; CO2CH2CH3 ×2, 4.19, q; 4-pyridyl proton 8.17, m; 6-pyridyl proton, 8.57, m; The reaction mixture was partitioned between water and chloroform the chloroform extract was dried treated with charcoal filtered through a silica bed evaporated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-methyl-3-nitro-pyridine (20 g) was reacted with 2-(3-cyanopropyl)malonic acid diethyl ester under conditions analogous to those in Example 1(a). The reaction mixture was partitioned between water and chloroform, the chloroform extract was dried, treated with charcoal and filtered through a silica bed and then evaporated to dryness to give 2-[4-cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine (18.3 g) as a yellow oil. N.M.R. (CDCl3) assignment, δ(p.p.m.), multiplicity; CO2CH2CH3 ×2, 1.2, t; --CH2CH2CH2CN, 1.3-2.0, m; --CH2CN, 2.37, m; 5-methylpyridyl, 2.49, s; CO2CH2CH3 ×2, 4.19, q; 4-pyridyl proton 8.17, m; 6-pyridyl proton, 8.57, m; The reaction mixture was partitioned between water and chloroform the chloroform extract was dried treated with charcoal filtered through a silica bed evaporated to dryness

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 6 g of diethyl 2-(3-cyanopropyl)malonate are added dropwise, at -10° C., to a suspension of 3 g of LiAlH4 in 100 ml of dry diethyl ether under N2. The mixture is slowly warmed to room temperature and then refluxed for 3 h. After renewed cooling to -10° C., the excess hydride is decomposed with water. The precipitate is removed on a frit and washed several times with diethyl ether. The ether solution is dried over MgSO4, filtered and evaporated in a rotary evaporator. Yield 0.66 g of 2-(4-aminobutyl)-1,3-propanediol, detectable in the 1H NMR and by C and H analysis. Glassy solid, melting point 126° C. (honey-like above 60° C.). refluxed for 3 h After renewed cooling to -10° C. The precipitate is removed on a frit washed several times with diethyl ether The ether solution is dried over MgSO4 filtered evaporated in a rotary evaporator Glassy solid, melting point 126° C. (honey-like above 60° C.)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-methyl-3-nitro-pyridine (20 g) was reacted with 2-(3-cyanopropyl)malonic acid diethyl ester under conditions analogous to those in Example 1(a). The reaction mixture was partitioned between water and chloroform, the chloroform extract was dried, treated with charcoal and filtered through a silica bed and then evaporated to a dryness to give 2-[4-cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine (18.3 g) as a yellow oil. The reaction mixture was partitioned between water and chloroform the chloroform extract was dried treated with charcoal filtered through a silica bed evaporated to a dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-methyl-3-nitro-pyridine (20 g) was reacted with 2-(3-cyanopropyl)malonic acid diethyl ester under conditions analogous to those in Example 1(a). The reaction mixture was partitioned between water and chloroform, the chloroform extract was dried, treated with charcoal and filtered through a silica bed and then evaporated to dryness to give 2-[4-cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine (18.3 g) as a yellow oil. N.M.R. (CDCl3) assignment, δ(p.p.m.), multiplicity; CO2CH2CH3 ×2, 1.2, t; --CH2CH2CH2CN, 1.3-2.0, m; --CH2CN, 2.37, m; 5-methylpyridyl, 2.49, s; CO2CH2CH3 ×2, 4.19, q; 4-pyridyl proton 8.17, m; 6-pyridyl proton, 8.57, m; The reaction mixture was partitioned between water and chloroform the chloroform extract was dried treated with charcoal filtered through a silica bed evaporated to dryness

反応条件: temp:0.00; pressure:0.00; stir: