2-(1H-indol-2-yl)ethanol

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

Procedure: Ester 4-1 (0.54 g, 2.6 mmol) was dissolved in 13 mL CH2Cl2 at -78°, and DIBAL (1M in CH2Cl2, 5.8 ml, 5.8 mmol) was added dropwise. The mixture was stirred at -78° for 15 min then warmed to RT for 30 min and quenched in sat. aqueous Na/K tartrate. This solution was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated. Flash chromatography (silica 50% EtOAc/hexane) provided 4-2 as a brown oil. Rf 0.38 (silica, 50% EtOAc/hexane). quenched in sat. aqueous Na/K tartrate This solution was extracted with EtOAc The organic layer was washed with brine dried (Na2SO4) concentrated

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

Procedure: Ester 4-1 (0.54 g, 2.6 mmol) was dissolved in 13 mL CH2Cl2 at -78°, and DIBAL (1M in CH2Cl2, 5.8 ml, 5.8 mmol) was added dropwise. The mixture was stirred at -78° for 15 min then warmed to RT for 30 min and quenched in sat. aqueous Na/K tartrate. This solution was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated. Flash chromatography (silica 50% EtOAc/hexane) provided 4-2 as a brown oil. Rf 0.38 (silica, 50% EtOAc/hexane). quenched in sat. aqueous Na/K tartrate This solution was extracted with EtOAc The organic layer was washed with brine dried (Na2SO4) concentrated

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

Procedure: Sodium cyanoborohydride (63 g) is added in portions to a stirred solution of 2-(2-hydroxyethyl)indole (43 g) in acetic acid (750 cc), whilst cooling the reaction mixture with a bath of cold water so as not to exceed 20° C. The mixture is stirred for 24 hours at this temperature. It is then concentrated to about 100 cc at 50° C. under reduced pressure (20 mm Hg). The residue is taken up in a mixture of water and ice (500 cc), the resulting mixture is rendered alkaline to pH 10 with an aqueous solution of sodium hydroxide and extraction is carried out with diethyl ether (3×300 cc). The organic extracts are combined, washed with water (50 cc), dried over magnesium sulphate and filtered and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg). 2-(2-Hydroxyethyl)indoline (43 g) is obtained in the form of a yellow oil (mass spectrum m/e=163). to exceed 20° C It is then concentrated to about 100 cc at 50° C. under reduced pressure (20 mm Hg) The residue is taken up in a mixture of water and ice (500 cc) with an aqueous solution of sodium hydroxide and extraction washed with water (50 cc) dried over magnesium sulphate filtered the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg)

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

Procedure: Ester 4-1 (0.54 g, 2.6 mmol) was dissolved in 13 mL CH2Cl2 at -78°, and DIBAL (1M in CH2Cl2, 5.8 ml, 5.8 mmol) was added dropwise. The mixture was stirred at -78° for 15 min then warmed to RT for 30 min and quenched in sat. aqueous Na/K tartrate. This solution was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated. Flash chromatography (silica 50% EtOAc/hexane) provided 4-2 as a brown oil. quenched in sat. aqueous Na/K tartrate This solution was extracted with EtOAc The organic layer was washed with brine dried (Na2SO4) concentrated

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

Procedure: Ester 4-1 (0.54 g, 2.6 mmol) was dissolved in 13 mL CH2Cl2 at -78°, and DIBAL (1M in CH2Cl2, 5.8 ml, 5.8 mmol) was added dropwise. The mixture was stirred at -78° for 15 min then warmed to RT for 30 min and quenched in sat. aqueous Na/K tartrate. This solution was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated. Flash chromatography (silica 50% EtOAc/hexane) provided 4-2 as a brown oil. Rf 0.38 (silica, 50% EtOAc/hexane). quenched in sat. aqueous Na/K tartrate This solution was extracted with EtOAc The organic layer was washed with brine dried (Na2SO4) concentrated

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

Procedure: Sodium cyanoborohydride (63 g) is added in portions to a stirred solution of 2-(2-hydroxyethyl)indole (43 g) in acetic acid (750 cc), whilst cooling the reaction mixture with a bath of cold water so as not to exceed 20° C. The mixture is stirred for 24 hours at this temperature. It is then concentrated to about 100 cc at 50° C. under reduced pressure (20 mm Hg). The residue is taken up in a mixture of water and ice (500 cc), the resulting mixture is rendered alkaline to pH 10 with an aqueous solution of sodium hydroxide and extraction is carried out with diethyl ether (3×300 cc). The organic extracts are combined, washed with water (50 cc), dried over magnesium sulphate and filtered and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg). 2-(2-Hydroxyethyl)indoline (43 g) is obtained in the form of a yellow oil (mass spectrum m/e=163). to exceed 20° C It is then concentrated to about 100 cc at 50° C. under reduced pressure (20 mm Hg) The residue is taken up in a mixture of water and ice (500 cc) with an aqueous solution of sodium hydroxide and extraction washed with water (50 cc) dried over magnesium sulphate filtered the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg)