2-amino-1-(1-benzofuran-2-yl)ethanol

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:

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

Procedure: Trimethylsilylcyanide (1.63 g, 2 ml) was added to a solution of 2-formylbenzofuran (2.0 g), (prepared as described in French Pat. No. 1.537.206) and a trace of zinc iodide in dry ether (50 ml) at 0° under nitrogen. The reaction mixture was stirred under nitrogen at ambient temperature for 10 h. This solution was then added dropwise to a suspension of lithium aluminium hydride (0.63 g) in dry ether under nitrogen. The mixture was heated under reflux for 1 h at the end of the addition. The reaction mixture was cooled; water (0.63 ml), 2 M sodium hydroxide (0.63 ml) and more water (1.89 ml) added, the reaction mixture filtered, the residue washed with chloroform and the combined solvents evaporated to give 2-(2-benzofuranyl)-2-hydroxyethanamine, (1.58 g). (prepared at 0° The mixture was heated under reflux for 1 h at the end of the addition The reaction mixture was cooled the reaction mixture filtered the residue washed with chloroform the combined solvents evaporated

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

Procedure: This compound was prepared in an identical manner to the compound described in Example 2 using 2-(2-benzofuranyl)-2-hydroxyethanamine (1.65 g) and 1-(4-methoxyphenyl)propan-2-one (1.53 g). Chromatography of the residual oil on Kieselgel 60 (4% methanol in dichloromethane) gave the title compound, m.p. 75°-85° (Et2O-hexane) as a 44:56 mixture of diastereoisomers. This compound was prepared in an identical manner to the compound

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

Procedure: This was prepared in an identical manner to the compound described in Example 2 using 2-(2-benzofuranyl)-2-hydroxyethanamine (3.51 g) and 1-(4-benzyloxyphenyl)propan-2-one (4.75 g). Chromatography of the residual oily solid on Kieselgel 60 (4% methanol in dichloromethane) gave the title compound, m.p. 111°-122°, as a 20:80 mixture of diastereoisomers. This was prepared in an identical manner to the compound

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

Procedure: A mixture of 1-(4-carbomethoxymethoxyphenyl)-propan-2-one (1 g) and 2-(2-benzofuranyl)-2-hydroxyethanamine (0.8 g) in benzene (80 ml) was boiled under reflux for one hour, with azeotropic removal of water, using a Dean and Stark head. The solution was evaporated, the residue dissolved in methanol (80 ml), cooled in ice, and excess sodium borohydride added. The solution was stirred at ambient temperature for 1 hour, heated under reflux for one hour, the methanol evaporated and the residue partitioned between water and ethyl acetate. The dried organic extract was evaporated to give an oil which was chromatographed on silica gel in 4% methanol/dichloromethane. The resulting oil was treated with ethereal hydrogen chloride to give the title compound as the hydrochloride salt hemi-hydrate, isolated as a 50:50 mixture of diastereoisomers. (mpt 56°-65°) (Ethyl Acetate-Ether). The solution was evaporated the residue dissolved in methanol (80 ml) cooled in ice excess sodium borohydride added heated under reflux for one hour the methanol evaporated the residue partitioned between water and ethyl acetate The dried organic extract was evaporated to give an oil which was chromatographed on silica gel in 4% methanol/dichloromethane The resulting oil was treated with ethereal hydrogen chloride

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

Procedure: A mixture of 2-(2-benzofuranyl)-2-hydroxyethanamine (1.75 g), 3-(4-methylphenyl)-1-(4-methylphenylsulphonyloxy) propane (3.0 g) and triethylamine (1.5 g) was stirred in dimethylsulphoxide for 2 days at ambient temperature. The mixture was poured into water, extracted with ether and the ether layers dried. Removal of the solvent gave an oil which was crystallised and recrystallised from ether to give N-[3-(4-methylphenyl)propyl]-2-(2-benzofuranyl)-2-hydroxyethanamine m.p. 118°-119°. extracted with ether the ether layers dried Removal of the solvent gave an oil which was crystallised recrystallised from ether

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

Procedure: By a method analogous to that described in Example 2 but using 2-(2-benzofuranyl)-2-hydroxyethanamine (4.54 g) and 1-(4-[3-carbomethoxypropoxy]phenyl)propan-2-one (6.41 g), N-[2-(4-(3-carbomethoxyphenoxy)phenyl)-1-methylphenyl]-2-(2-benzofuranyl)-2-hydroxyethanamine was prepared, m.p. 63°-70° (Et2O) as a 37:63 mixture of diastereoisomers. was prepared