benzyl N-(2,2-diethoxyethyl)carbamate

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

Procedure: A solution of 3,4-dihydroxyphenethylamine hydrochloride (2.17 g) and N-benzyloxycarbonylaminoacetaldehyde diethyl acetal (4.0 g) in a mixture of n-butyl alcohol (20 ml) and water (3.5 ml) was refluxed for 4.5 hours. After the reaction, the solvent was distilled off under reduced pressure. To the residue were added water (15 ml) and sodium acetate. A precipitating oil was separated from the aqueous layer and chloroform was added thereto. The mixture was allowed to stand to give crystals. The crystals were collected by filtration, washed with chloroform and recrystallized twice from a mixture of methanol and ether to give 1(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline acetate (1.2 g), mp 158° to 162° C. (dec). was refluxed for 4.5 hours After the reaction the solvent was distilled off under reduced pressure To the residue were added water (15 ml) and sodium acetate A precipitating oil was separated from the aqueous layer and chloroform was added to give crystals The crystals were collected by filtration washed with chloroform recrystallized twice from a mixture of methanol and ether

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

Procedure: A solution of 3,4-dihydroxyphenethylamine hydrochloride (2.17 g) and N-benzyloxycarbonylaminoacetaldehyde diethyl acetal (4.0 g) in a mixture of n-butyl alcohol (20 ml) and water (3.5 ml) was refluxed for 4.5 hours. After the reaction, the solvent was distilled off under reduced pressure. To the residue were added water (15 ml) and sodium acetate. A precipitating oil was separated from the aqueous layer and chloroform was added thereto. The mixture was allowed to stand to give crystals. The crystals were collected by filtration, washed with chloroform and recrystallized twice from a mixture of methanol and ether to give 1(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline acetate (1.2 g), mp 158° to 162° C. (dec). was refluxed for 4.5 hours After the reaction the solvent was distilled off under reduced pressure To the residue were added water (15 ml) and sodium acetate A precipitating oil was separated from the aqueous layer and chloroform was added to give crystals The crystals were collected by filtration washed with chloroform recrystallized twice from a mixture of methanol and ether

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

Procedure: A solution of 3,4-dihydroxyphenethylamine hydrochloride (2.17 g) and N-benzyloxycarbonylaminoacetaldehyde diethyl acetal (4.0 g) in a mixture of n-butyl alcohol (20 ml) and water (3.5 ml) was refluxed for 4.5 hours. After the reaction, the solvent was distilled off under reduced pressure. To the residue were added water (15 ml) and sodium acetate. A precipitating oil was separated from the aqueous layer and chloroform was added thereto. The mixture was allowed to stand to give crystals. The crystals were collected by filtration, washed with chloroform and recrystallized twice from a mixture of methanol and ether to give 1(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline acetate (1.2 g), mp 158° to 162° C. (dec). was refluxed for 4.5 hours After the reaction the solvent was distilled off under reduced pressure To the residue were added water (15 ml) and sodium acetate A precipitating oil was separated from the aqueous layer and chloroform was added to give crystals The crystals were collected by filtration washed with chloroform recrystallized twice from a mixture of methanol and ether

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

Procedure: A solution of 3,4-dihydroxyphenethylamine hydrochloride (2.17 g) and N-benzyloxycarbonylaminoacetaldehyde diethyl acetal (4.0 g) in a mixture of n-butyl alcohol (20 ml) and water (3.5 ml) was refluxed for 4.5 hours. After the reaction, the solvent was distilled off under reduced pressure. To the residue were added water (15 ml) and sodium acetate. A precipitating oil was separated from the aqueous layer and chloroform was added thereto. The mixture was allowed to stand to give crystals. The crystals were collected by filtration, washed with chloroform and recrystallized twice from a mixture of methanol and ether to give 1(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline acetate (1.2 g), mp 158° to 162° C. (dec). was refluxed for 4.5 hours After the reaction the solvent was distilled off under reduced pressure To the residue were added water (15 ml) and sodium acetate A precipitating oil was separated from the aqueous layer and chloroform was added to give crystals The crystals were collected by filtration washed with chloroform recrystallized twice from a mixture of methanol and ether

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

Procedure: A solution of 3,4-dihydroxyphenethylamine hydrochloride (2.17 g) and N-benzyloxycarbonylaminoacetaldehyde diethyl acetal (4.0 g) in a mixture of n-butyl alcohol (20 ml) and water (3.5 ml) was refluxed for 4.5 hours. After the reaction, the solvent was distilled off under reduced pressure. To the residue were added water (15 ml) and sodium acetate. A precipitating oil was separated from the aqueous layer and chloroform was added thereto. The mixture was allowed to stand to give crystals. The crystals were collected by filtration, washed with chloroform and recrystallized twice from a mixture of methanol and ether to give 1(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline acetate (1.2 g), mp 158° to 162° C. (dec). was refluxed for 4.5 hours After the reaction the solvent was distilled off under reduced pressure To the residue were added water (15 ml) and sodium acetate A precipitating oil was separated from the aqueous layer and chloroform was added to give crystals The crystals were collected by filtration washed with chloroform recrystallized twice from a mixture of methanol and ether

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

Procedure: An aqueous solution (400 ml) of sodium carbonate (31.8 g) and carbobenzoxy chloride (51.2 g) were added to a solution of 2,2-diethoxyethylamine (42.0 g) in ethyl acetate (300 ml) under ice-cooling, and the mixture was stirred for 6 hours. After separating the mixture into layers, the organic layer was washed successively with 0.5N hydrochloric acid, an aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried and concentrated to give pale orange oily benzyl 2,2-diethoxyethylcarbamate (78.6 g). cooling After separating the mixture into layers the organic layer was washed successively with 0.5N hydrochloric acid an aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried concentrated

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

Procedure: An aqueous solution (400 ml) of sodium carbonate (31.8 g) and carbobenzoxy chloride (51.2 g) were added to a solution of 2,2-diethoxyethylamine (42.0 g) in ethyl acetate (300 ml) under ice-cooling, and the mixture was stirred for 6 hours. After separating the mixture into layers, the organic layer was washed successively with 0.5N hydrochloric acid, an aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried and concentrated to give pale orange oily benzyl 2,2-diethoxyethylcarbamate (78.6 g). cooling After separating the mixture into layers the organic layer was washed successively with 0.5N hydrochloric acid an aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried concentrated

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

Procedure: An aqueous solution (400 ml) of sodium carbonate (31.8 g) and carbobenzoxy chloride (51.2 g) were added to a solution of 2,2-diethoxyethylamine (42.0 g) in ethyl acetate (300 ml) under ice-cooling, and the mixture was stirred for 6 hours. After separating the mixture into layers, the organic layer was washed successively with 0.5N hydrochloric acid, an aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried and concentrated to give pale orange oily benzyl 2,2-diethoxyethylcarbamate (78.6 g). cooling After separating the mixture into layers the organic layer was washed successively with 0.5N hydrochloric acid an aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried concentrated

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

Procedure: To a solution of 50 g of N-benzyl-tryptamine hydrochloride (i.e., 3-(2-(benzylamino)-ethyl)indole hydrochloride) in 500 ml of methanol-water (4:1) are added 57.9 g of N-benzyloxycarbonyl-aminoacetaldehyde diethylacetal and 25 ml of 10% hydrochloric acid, and the mixture is refluxed for 16 hours. After the reaction, the reaction mixture is evaporated under reduced pressure to remove solvent, and the resultant crystals are collected by filtration. After being washed with water and ether, said crystals are added to a saturated sodium bicarbonate solution, and then extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove solvent. The residue (oil, 60 g) is purified by silica gel chromatography (Solvent: chloroform-methanol (20:1)). 46 g of 1,2,3,4-tetrahydro-1-((N-benzyloxycarbonylamino)methyl)-2-benzyl-β-carboline are thereby obtained as a caramel. Yield: 62% the mixture is refluxed for 16 hours After the reaction the reaction mixture is evaporated under reduced pressure to remove solvent the resultant crystals are collected by filtration After being washed with water and ether are added to a saturated sodium bicarbonate solution extracted with ethyl acetate The extract is washed with water dried evaporated to remove solvent The residue (oil, 60 g) is purified by silica gel chromatography (Solvent: chloroform-methanol (20:1))

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

Procedure: A solution of 3,4-dihydroxyphenethylamine hydrochloride (2.17 g) and N-benzyloxycarbonylaminoacetaldehyde diethyl acetal (4.0 g) in a mixture of n-butyl alcohol (20 ml) and water (3.5 ml) was refluxed for 4.5 hours. After the reaction, the solvent was distilled off under reduced pressure. To the residue were added water (15 ml) and sodium acetate. A precipitating oil was separated from the aqueous layer and chloroform was added thereto. The mixture was allowed to stand to give crystals. The crystals were collected by filtration, washed with chloroform and recrystallized twice from a mixture of methanol and ether to give 1(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline acetate (1.2 g), mp 158° to 162° C. (dec). was refluxed for 4.5 hours After the reaction the solvent was distilled off under reduced pressure To the residue were added water (15 ml) and sodium acetate A precipitating oil was separated from the aqueous layer and chloroform was added to give crystals The crystals were collected by filtration washed with chloroform recrystallized twice from a mixture of methanol and ether