diethyl 2-(3-oxopropyl)propanedioate

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

Procedure: First, 100 ml acrolein was added to a solution of 180 g diethyl bromomalonate, 14 g tributylamine, and 600 ml ethanol while cooling in an ice bath. After 2-3 hours, an additional 1.5 g tributylamine and 20 ml acrolein was added. The stirring was continued for an additional 1 to 2 hours without additional cooling. The reaction mixture was neutralized with 7 ml glacial acetic acid and the ethanol and unreacted acrolein were removed on a rotary evaporator. The residue was diluted with 500 ml benzene and washed with 3× 100 ml H2O and 2× 100 ml saturated NaCl solution. The benzene solution was dired over CaSO4 and rotary evaporated to yield 207 g of yellow oil which was indicated to be 48% product by glc. while cooling in an ice bath The stirring was continued for an additional 1 to 2 hours without additional cooling the ethanol and unreacted acrolein were removed on a rotary evaporator The residue was diluted with 500 ml benzene washed with 3× 100 ml H2O and 2× 100 ml saturated NaCl solution rotary evaporated

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

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

Procedure: First, 100 ml acrolein was added to a solution of 180 g diethyl bromomalonate, 14 g tributylamine, and 600 ml ethanol while cooling in an ice bath. After 2-3 hours, an additional 1.5 g tributylamine and 20 ml acrolein was added. The stirring was continued for an additional 1 to 2 hours without additional cooling. The reaction mixture was neutralized with 7 ml glacial acetic acid and the ethanol and unreacted acrolein were removed on a rotary evaporator. The residue was diluted with 500 ml benzene and washed with 3×100 ml H2O and 2×100 ml saturated NaCl solution. The benzene solution was dried over CaSO4 and rotary evaporated to yield 207 g of yellow oil which was indicated to be 48% product by glc. while cooling in an ice bath The stirring was continued for an additional 1 to 2 hours without additional cooling the ethanol and unreacted acrolein were removed on a rotary evaporator The residue was diluted with 500 ml benzene washed with 3×100 ml H2O and 2×100 ml saturated NaCl solution The benzene solution was dried over CaSO4 rotary evaporated

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

Procedure: 1.78 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole) and 3.1 g of 4,4-bis(ethoxycarbonyl)-butanal were treated in the same manner as described in Example 21-(1). 2.1 g of 1,2,3,4-tetrahydro-1-[3,3-bis-(ethoxycarbonyl)propyl]-2-methyl-β-carboline were thereby obtained. Yield: 55.0%

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

Procedure: First, 100 ml acrolein was added to a solution of 180 g diethyl bromomalonate, 14 g tributylamine, and 600 ml ethanol while cooling in an ice bath. After 2-3 hours, an additional 1.5 g tributylamine and 20 ml acrolein was added. The stirring was continued for an additional 1 to 2 hours without additional cooling. The reaction mixture was neutralized with 7 ml glacial acetic acid and the ethanol and unreacted acrolein were removed on a rotary evaporator. The residue was diluted with 500 ml benzene and washed with 3×100 ml H2O and 2×100 ml saturated NaCl solution. The benzene solution was dried over CaSO4 and rotary evaporated to yield 207 g of yellow oil which was indicated to be 48% product by glc. while cooling in an ice bath The stirring was continued for an additional 1 to 2 hours without additional cooling the ethanol and unreacted acrolein were removed on a rotary evaporator The residue was diluted with 500 ml benzene washed with 3×100 ml H2O and 2×100 ml saturated NaCl solution The benzene solution was dried over CaSO4 rotary evaporated

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

Procedure: First, 100 ml acrolein was added to a solution of 180 g diethyl bromomalonate, 14 g tributylamine, and 600 ml ethanol while cooling in an ice bath. After 2-3 hours, an additional 1.5 g tributylamine and 20 ml acrolein was added. The stirring was continued for an additional 1 to 2 hours without additional cooling. The reaction mixture was neutralized with 7 ml glacial acetic acid and the ethanol and unreacted acrolein were removed on a rotary evaporator. The residue was diluted with 500 ml benzene and washed with 3×100 ml H2O and 2×100 ml saturated NaCl solution. The benzene solution was dried over CaSO4 and rotary evaporated to yield 207 g of yellow oil which was indicated to be 48% product by glc. while cooling in an ice bath The stirring was continued for an additional 1 to 2 hours without additional cooling the ethanol and unreacted acrolein were removed on a rotary evaporator The residue was diluted with 500 ml benzene washed with 3×100 ml H2O and 2×100 ml saturated NaCl solution The benzene solution was dried over CaSO4 rotary evaporated

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

Procedure: First, 100 ml acrolein was added to a solution of 180 g diethyl bromomalonate, 14 g tributylamine, and 600 ml ethanol while cooling in an ice bath. After 2-3 hours, an additional 1.5 g tributylamine and 20 ml acrolein was added. The stirring was continued for an additional 1 to 2 hours without additional cooling. The reaction mixture was neutralized with 7 ml glacial acetic acid and the ethanol and unreacted acrolein were removed on a rotary evaporator. The residue was diluted with 500 ml benzene and washed with 3× 100 ml H2O and 2× 100 ml saturated NaCl solution. The benzene solution was dired over CaSO4 and rotary evaporated to yield 207 g of yellow oil which was indicated to be 48% product by glc. while cooling in an ice bath The stirring was continued for an additional 1 to 2 hours without additional cooling the ethanol and unreacted acrolein were removed on a rotary evaporator The residue was diluted with 500 ml benzene washed with 3× 100 ml H2O and 2× 100 ml saturated NaCl solution rotary evaporated

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

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

Procedure: First, 100 ml acrolein was added to a solution of 180 g diethyl bromomalonate, 14 g tributylamine, and 600 ml ethanol while cooling in an ice bath. After 2-3 hours, an additional 1.5 g tributylamine and 20 ml acrolein was added. The stirring was continued for an additional 1 to 2 hours without additional cooling. The reaction mixture was neutralized with 7 ml glacial acetic acid and the ethanol and unreacted acrolein were removed on a rotary evaporator. The residue was diluted with 500 ml benzene and washed with 3× 100 ml H2O and 2× 100 ml saturated NaCl solution. The benzene solution was dired over CaSO4 and rotary evaporated to yield 207 g of yellow oil which was indicated to be 48% product by glc. while cooling in an ice bath The stirring was continued for an additional 1 to 2 hours without additional cooling the ethanol and unreacted acrolein were removed on a rotary evaporator The residue was diluted with 500 ml benzene washed with 3× 100 ml H2O and 2× 100 ml saturated NaCl solution rotary evaporated

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

Procedure: 1.78 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole) and 3.1 g of 4,4-bis(ethoxycarbonyl)-butanal were treated in the same manner as described in Example 21-(1). 2.1 g of 1,2,3,4-tetrahydro-1-[3,3-bis-(ethoxycarbonyl)propyl]-2-methyl-β-carboline were thereby obtained. Yield: 55.0%

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

Procedure: First, 100 ml acrolein was added to a solution of 180 g diethyl bromomalonate, 14 g tributylamine, and 600 ml ethanol while cooling in an ice bath. After 2-3 hours, an additional 1.5 g tributylamine and 20 ml acrolein was added. The stirring was continued for an additional 1 to 2 hours without additional cooling. The reaction mixture was neutralized with 7 ml glacial acetic acid and the ethanol and unreacted acrolein were removed on a rotary evaporator. The residue was diluted with 500 ml benzene and washed with 3×100 ml H2O and 2×100 ml saturated NaCl solution. The benzene solution was dried over CaSO4 and rotary evaporated to yield 207 g of yellow oil which was indicated to be 48% product by glc. while cooling in an ice bath The stirring was continued for an additional 1 to 2 hours without additional cooling the ethanol and unreacted acrolein were removed on a rotary evaporator The residue was diluted with 500 ml benzene washed with 3×100 ml H2O and 2×100 ml saturated NaCl solution The benzene solution was dried over CaSO4 rotary evaporated