3-(dodecylamino)propane-1,2-diol

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedures of Ulsperger et al., J. Prakt. Chemie, Vol. 27, pp. 195-212 (1965), the disclosures of which are hereby incorporated herein by reference in their entirety, were substantially followed. Specifically, 18.54 g laurylamine (0.1M) and 7.4 g glycidol (0.1M) were mixed in 150 ml methanol at 60° C. for 5 hours. The mixture was refluxed for 1 hour at 70° C. The methanol was then removed by rotary evaporation. The product was a solid, 15.3 g (59% yield). After recrystallization from hexane, LDP, was recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.). The methanol was then removed by rotary evaporation After recrystallization from hexane, LDP was recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedures of Ulsperger et al., J. Prakt. Chemie, Vol. 27, pp. 195-212 (1965), the disclosures of which are hereby incorporated herein by reference in their entirety, were substantially followed. Specifically, 18.54 g laurylamine (0.1M) and 7.4 g glycidol (0.1M) were mixed in 150 ml methanol at 60° C. for 5 hours. The mixture was refluxed for 1 hour at 70° C. The methanol was then removed by rotary evaporation. The product was a solid, 15.3 g (59% yield). After recrystallization from hexane, LDP, was recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.). The methanol was then removed by rotary evaporation After recrystallization from hexane, LDP was recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedures of Ulsperger et al., J. Prakt. Chemie, Vol. 27, pp. 195-212 (1965), the disclosures of which are hereby incorporated herein by reference in their entirety, were substantially followed. Specifically, 18.54 g laurylamine (0.1M) and 7.4 g glycidol (0.1M) were mixed in 150 ml methanol at 60° C. for 5 hours. The mixture was refluxed for 1 hour at 70° C. The methanol was then removed by rotary evaporation. The product was a solid, 15.3 g (59% yield). After recrystallization from hexane, LDP, was recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.). The methanol was then removed by rotary evaporation After recrystallization from hexane, LDP was recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedures of Ulsperger et al., J. Prakt. Chemie, Vol. 27, pp. 195-212 (1965), the disclosures of which are hereby incorporated herein by reference in their entirety, were substantially followed. Specifically, 18.54 g laurylamine (0.1M) and 7.4 g glycidol (0.1M) were mixed in 150 ml methanol at 60° C. for 5 hours. The mixture was refluxed for 1 hour at 70° C. The methanol was then removed by rotary evaporation. The product was a solid, 15.3 g (59% yield). After recrystallization from hexane, LDP, was recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.). The methanol was then removed by rotary evaporation After recrystallization from hexane, LDP was recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.)

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

Procedure: N-(2,3-dihydroxypropyl)-N-dodecylamine (1.00 g, 0.0039 mole) and potassium hydroxide (0.01 g, 0.18 mmole) were heated to 85° C. under vacuum and methyl-2-hydroxyhexadecanoate (1.12 g, 0.0039 mole) was heated and added dropwise to the reaction. The reaction was heated under vacuum for 6 hours. A waxy off-white solid was obtained (crude yield=1.9 g). The waxy solid was recrystalized from hot hexane (yield=1.26 g). was heated added dropwise to the reaction The reaction was heated under vacuum for 6 hours A waxy off-white solid was obtained (crude yield=1.9 g) The waxy solid was recrystalized from hot hexane (yield=1.26 g)

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

Procedure: N-(2,3-dihydroxypropyl)-N-dodecylamine (1.0 g, 0.0039 mole) and potassium hydroxide (0.01 g, 0.18 mmole) were heated to 85° C. under vacuum and methyl 2-hydroxyoctanoate (0.6718 g, 0.0039 mole) was added dropwise to the reaction. The reaction was heated under vacuum for 5 hours. A waxy off-white solid was obtained (crude yield=1.38 g). The waxy solid was recrystalized from hot hexane (yield=0.44 g). was added dropwise to the reaction The reaction was heated under vacuum for 5 hours A waxy off-white solid was obtained (crude yield=1.38 g) The waxy solid was recrystalized from hot hexane (yield=0.44 g)

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

Procedure: N-(2,3-dihydroxypropyl)-N-dodecylamine (0.50 g, 0.0019 mole) and potassium hydroxide (0.01 g, 0.18 mmole) were heated to 85° C. under vacuum. Methyl palmitate (0.57 g, 0.0021 mole) was heated and added dropwise to the reaction. The reaction was heated under vacuum for 6 hours. A waxy off-white solid was obtained (crude yield=0.92 g) The waxy solid was recrystalized from hot hexane (yield=0.6 g). added dropwise to the reaction The reaction was heated under vacuum for 6 hours A waxy off-white solid was obtained (crude yield=0.92 g) The waxy solid was recrystalized from hot hexane (yield=0.6 g)

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

Procedure: N-(2,3-dihydroxypropyl)-N-dodecylamine (0.50 g, 0.0019 mole) and potassium hydroxide (0.01 g, 0.18 mmole) were heated to 85° C. under vacuum. Methyl palmitate (0.57 g, 0.0021 mole) was heated and added dropwise to the reaction. The reaction was heated under vacuum for 6 hours. A waxy off-white solid was obtained (crude yield=0.92 g) The waxy solid was recrystalized from hot hexane (yield=0.6 g). added dropwise to the reaction The reaction was heated under vacuum for 6 hours A waxy off-white solid was obtained (crude yield=0.92 g) The waxy solid was recrystalized from hot hexane (yield=0.6 g)

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

Procedure: N-(2,3-dihydroxypropyl)-N-dodecylamine (0.50 g, 0.0019 mole) and potassium hydroxide (0.01 g, 0.18 mmole) were heated to 85° C. under vacuum. Methyl palmitate (0.57 g, 0.0021 mole) was heated and added dropwise to the reaction. The reaction was heated under vacuum for 6 hours. A waxy off-white solid was obtained (crude yield=0.92 g) The waxy solid was recrystalized from hot hexane (yield=0.6 g). added dropwise to the reaction The reaction was heated under vacuum for 6 hours A waxy off-white solid was obtained (crude yield=0.92 g) The waxy solid was recrystalized from hot hexane (yield=0.6 g)

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

Procedure: Dodecylamine (25.02 g, 0.13 mole) was heated to 85° C. Glycidol (10 g, 0.13 mole) was added dropwise. The reaction solution was heated under nitrogen for 3 hours and was stirred overnight at room temperature. A white solid was obtained (crude yield=33.27 g). The solid was recrystalized from hot hexane (crystallized 10.86 g). The reaction solution was heated under nitrogen for 3 hours A white solid was obtained (crude yield=33.27 g) The solid was recrystalized from hot hexane (crystallized 10.86 g)

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

Procedure: Dodecylamine (25.02 g, 0.13 moles) was heated at 85° C., and glycidol (10 g, 0.13 moles) was added dropwise. The reaction was heated under nitrogen for 3 hours then allowed to stir overnight. A white solid was recovered (crude yield=33.27 g), and the solid was recrystallized in hot hexane to give pure neosphingosine (yield=10.86 g). The reaction was heated under nitrogen for 3 hours A white solid was recovered (crude yield=33.27 g) the solid was recrystallized in hot hexane to give pure neosphingosine (yield=10.86 g)

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

Procedure: Dodecylamine (25.02 g, 0.13 moles) was heated at 85° C., and glycidol (10 g, 0.13 moles) was added dropwise. The reaction was heated under nitrogen for 3 hours then allowed to stir overnight. A white solid was recovered (crude yield=33.27 g), and the solid was recrystallized in hot hexane to give pure neosphingosine (yield=10.86 g). The reaction was heated under nitrogen for 3 hours A white solid was recovered (crude yield=33.27 g) the solid was recrystallized in hot hexane to give pure neosphingosine (yield=10.86 g)