octyl carbonochloridate

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

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

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

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

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

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

Procedure: 20 g (224.46 mmol) of β-alanine were dissolved in 225 ml of 1N sodium hydroxide solution. 44 ml of octyl chloroformate were then added dropwise, while keeping the pH of the reaction medium above 9 by simultaneous addition of one molar equivalent of 1N sodium hydroxide. After stirring for 6 hours at room temperature, the mixture was acidified with about 1.1 molar equivalents of 3N hydrochloric acid solution. The heterogeneous mixture was extracted with 300 ml of ethyl acetate. The organic phase was washed with 3 times 80 ml of water, dried and then evaporated to dryness. The solid residue was taken up in heptane and then filtered and dried. 51 g of a white product were obtained (yield of 93%). The heterogeneous mixture was extracted with 300 ml of ethyl acetate The organic phase was washed with 3 times 80 ml of water dried evaporated to dryness filtered dried

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Octyl chloroformate (2.00 ml) was added dropwise to a solution of 2.15 g 2-(2-aminophenyl)-2,3-dihydro-1H-indole and 2.00 ml pyridine in 35 ml CH2Cl2 at 0° C. The solution was stirred five hours at 0° C. and then quenched with water. The organic layer was separated, washed with 5% HCl and saturated NaCl solution, dried (MgSO4), and concentrated to yield a solid. Purification by flash chromatography using CH2Cl2 /hexane (1:2) as eluent gave 1.74 g solid, m.p. 99°-102° C. quenched with water The organic layer was separated washed with 5% HCl and saturated NaCl solution dried (MgSO4) concentrated to yield a solid Purification by flash chromatography

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: n Butyllithium, 0.033 mol, is added to a suspension of 6.5g (0.033 mol) of 1,2,3,4-tetra -hydro-9-acridinamine (Petrow, V., Journal of the Chemical Society, pages 634 to 637 (1947)) in 200 ml of tetrahydrofuran at 0° C. The mixture is stirred at 0° C. for 20 minutes, the cooling bath removed and 6.36 g (0.033 mol) of octyl chloroformate added and the solution stirred over the weekend. Water, 200 ml, is added and the mixture extracted with ethyl acetate. The ethyl acetate layer is separated and evaporated to afford a yellow oil. Chromatography (elution with isopropanol-chloroform (5:95)) affords 6.59 g of octyl (1,2,3,4-tetrahydro-9-acridinyl)carbamate, as a yelIow solid; mp 96-99° C. at 0° C the cooling bath removed the solution stirred over the weekend the mixture extracted with ethyl acetate The ethyl acetate layer is separated evaporated to afford a yellow oil Chromatography (elution with isopropanol-chloroform (5:95))

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

Procedure: A solution of 2-amino-5-methylbenzoic acid (302 mg, 2 mmol) in pyridine (10 ml) was cooled to 0° C. and treated dropwise with octyl chloroformate (1.15 ml, 6 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 4 h. The pyridine was removed under vacuum and the residue dissolved in ethyl acetate (50 ml). This solution was washed with 1M HCl (10 ml) and brine (5 ml), dried (MgSO4) and the solvent removed in vacuo to afford a pale orange oily solid. Recrystallisation from hexane afforded the desired product as an off-white solid (144 mg, 25%); δH (400 MHz, DMSO-d6) 0.68 (3H, t, J 7, CH2CH3), 1.26-1.40 (10H, m, 5×CH2), 1.73 (2H, tt, J, J′7, OCH2CH2), 2.35 (3H, s, CH3), 4.35 (2H, t, J 7, OCH2), 7.34 (1H, d, J 8, Ph), 7.65 (1H, d, J 8, Ph), 7.83 (1H, s, Ph); m/z (ES+) 290 (MH+). The pyridine was removed under vacuum the residue dissolved in ethyl acetate (50 ml) This solution was washed with 1M HCl (10 ml) and brine (5 ml) dried (MgSO4) the solvent removed in vacuo to afford a pale orange oily solid Recrystallisation from hexane

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

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

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