2-aminopropane-1,3-diol;hydrochloride

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

Procedure: BOC-L-Ala (567 mg, 2 mMol) and HOBT.H2O (505 mg, 3.3 mMol) were dissolved in 5 ml CH2Cl2 and 5 ml DMF, then treated with 1,3-dicyclohexylcarbodiimide (DCC, 680 mg, 3.3 mMol). The resulting solution was stirred at RT for one hour, then treated dropwise with a solution that contained 421 mg (3.3 mMol) of serinol hydrochloride (Aldrich) and 333 mg (3.3 mMol) of N-methylmorpholine in 5 ml of DMF. The reaction mixture was stirred at RT for 20 hours, then treated with 0.5 ml of glacial acetic acid and stirred for another hour. The solid reaction by-products were removed by filtration and washed with 20 ml CH2Cl2. The combined filtrate and washings was concentrated to dryness on the rotary evaporator then further dried under high vacuum. The oily residue was taken up in 50 ml of H2O, cooled at 4° C. for several hours, then filtered. The filtrate was concentrated to dryness on the rotary evaporator, then further dried under high vacuum to yield the crude product as a yellow oil. treated dropwise with a solution that The reaction mixture was stirred at RT for 20 hours stirred for another hour The solid reaction by-products were removed by filtration washed with 20 ml CH2Cl2 The combined filtrate and washings was concentrated to dryness on the rotary evaporator then further dried under high vacuum cooled at 4° C. for several hours filtered The filtrate was concentrated to dryness on the rotary evaporator further dried under high vacuum

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of serinol hydrochloride (0.765 g, 6.00 mmol) in methanol (20 mL) was stirred with basic ion exchange resin for 10 minutes. The resin was filtered off and the filtrate concentrated to a colorless oil. To this was added (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.544 g, 2.00 mmol) and methanol (10 mL). The resulting solution was stirred in a Parr bomb at 80° C. overnight. 1N NaOH (2 mL) was added and the solvent evaporated. The residue was chromatrographed on silica gel. Title compound eluted with 20% methanol-chloroform; white powder after crystallization from acetonitrile-methanol (0.404 g, 63%), m.p. 160-162° C. The resin was filtered off the filtrate concentrated to a colorless oil the solvent evaporated Title compound eluted with 20% methanol-chloroform white powder after crystallization from acetonitrile-methanol (0.404 g, 63%), m.p. 160-162° C.

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

Procedure: BOC-L-Ala (567 mg, 2 mMol) and HOBT.H2O (505 mg, 3.3 mMol) were dissolved in 5 ml CH2Cl2 and 5 ml DMF, then treated with 1,3-dicyclohexylcarbodiimide (DCC, 680 mg, 3.3 mMol). The resulting solution was stirred at RT for one hour, then treated dropwise with a solution that contained 421 mg (3.3 mMol) of serinol hydrochloride (Aldrich) and 333 mg (3.3 mMol) of N-methylmorpholine in 5 ml of DMF. The reaction mixture was stirred at RT for 20 hours, then treated with 0.5 ml of glacial acetic acid and stirred for another hour. The solid reaction by-products were removed by filtration and washed with 20 ml CH2Cl2. The combined filtrate and washings was concentrated to dryness on the rotary evaporator then further dried under high vacuum. The oily residue was taken up in 50 ml of H2O, cooled at 4° C. for several hours, then filtered. The filtrate was concentrated to dryness on the rotary evaporator, then further dried under high vacuum to yield the crude product as a yellow oil. treated dropwise with a solution that The reaction mixture was stirred at RT for 20 hours stirred for another hour The solid reaction by-products were removed by filtration washed with 20 ml CH2Cl2 The combined filtrate and washings was concentrated to dryness on the rotary evaporator then further dried under high vacuum cooled at 4° C. for several hours filtered The filtrate was concentrated to dryness on the rotary evaporator further dried under high vacuum

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

Procedure: BOC-L-Ala (567 mg, 2 mMol) and HOBT.H2O (505 mg, 3.3 mMol) were dissolved in 5 ml CH2Cl2 and 5 ml DMF, then treated with 1,3-dicyclohexylcarbodiimide (DCC, 680 mg, 3.3 mMol). The resulting solution was stirred at RT for one hour, then treated dropwise with a solution that contained 421 mg (3.3 mMol) of serinol hydrochloride (Aldrich) and 333 mg (3.3 mMol) of N-methylmorpholine in 5 ml of DMF. The reaction mixture was stirred at RT for 20 hours, then treated with 0.5 ml of glacial acetic acid and stirred for another hour. The solid reaction by-products were removed by filtration and washed with 20 ml CH2Cl2. The combined filtrate and washings was concentrated to dryness on the rotary evaporator then further dried under high vacuum. The oily residue was taken up in 50 ml of H2O, cooled at 4° C. for several hours, then filtered. The filtrate was concentrated to dryness on the rotary evaporator, then further dried under high vacuum to yield the crude product as a yellow oil. treated dropwise with a solution that The reaction mixture was stirred at RT for 20 hours stirred for another hour The solid reaction by-products were removed by filtration washed with 20 ml CH2Cl2 The combined filtrate and washings was concentrated to dryness on the rotary evaporator then further dried under high vacuum cooled at 4° C. for several hours filtered The filtrate was concentrated to dryness on the rotary evaporator further dried under high vacuum

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

Procedure: Using the reductive amination procedure outlined in 1C, chrysene-6-carbaldehyde (1A) and 2-amino-1,3-propanediol hydrochloride (Sigma) gave 2-((6-chrysenylmethyl)amino)-1,3-propanediol methanesulfonate mp 208°-209°, (CH3OH/Et2O), (C,H,N,S).

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

Procedure: Using the reductive amination procedure outlined in 1C, chrysene-6-carbaldehyde (1A) and 2-amino-1,3-propanediol hyrochloride (Sigma) gave 2-((6-chrysenylmethyl)amino)-1,3-propanediol methanesulfonate mp 208°-209°, (CH3OH/Et2O), (C, H, N, S).

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

Procedure: Using the reductive amination procedure outlined in 1C, chrysene-6-carbaldehyde (1A) and 2-amino-1,3-propanediol hydrochloride (Simga) gave 2-((6-chrysenylmethyl)amino)-1,3-propanediol methanesulfonate mp 208°-209°, (CH3OH/Et2O), (C,H,N,S).

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

Procedure: Using the reductive amination procedure outlined in 1C, chrysene-6-carbaldehyde (1A) and 2-amino-1,3-propanediol hydrochloride (Sigma) gave 2-((6-chrysenylmethyl)amino)-1,3-propanediol methanesulfonate mp 208°-209°, (CH3OH/Et2O), (C, H, N, S).

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of serinol hydrochloride (0.765 g, 6.00 mmol) in methanol (20 mL) was stirred with basic ion exchange resin for 10 minutes. The resin was filtered off and the filtrate concentrated to a colorless oil. To this was added (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.544 g, 2.00 mmol) and methanol (10 mL). The resulting solution was stirred in a Parr bomb at 80° C. overnight. 1N NaOH (2 mL) was added and the solvent evaporated. The residue was chromatrographed on silica gel. Title compound eluted with 20% methanol-chloroform; white powder after crystallization from acetonitrile-methanol (0.404 g, 63%), m.p. 160-162° C. The resin was filtered off the filtrate concentrated to a colorless oil the solvent evaporated Title compound eluted with 20% methanol-chloroform white powder after crystallization from acetonitrile-methanol (0.404 g, 63%), m.p. 160-162° C.