1-amino-3-methoxypropan-2-ol

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: 5.0 g (47.6 mmol) of rac-1-amino-3-methoxypropan-2-ol were initially charged in THF (158 ml), and 7.36 ml (52.3 mmol) of benzyl chlorocarbonate, 24.85 ml (142.7 mmol) of N,N-diisopropyl ethyl amine and 1.16 g (9.5 mmol) of 4-dimethylaminopyridine were added. The reaction mixture was stirred at RT for 16 h. 3.7 ml (26.2 mmol) of benzyl chlorocarbonate and then 15 ml of DMF were added, and the reaction solution was stirred at RT overnight. The mixture was concentrated and diluted with ethyl acetate. The mixture was then washed with water, saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, filtered off and concentrated. The aqueous phase was concentrated, the residue was taken up in ethyl acetate, the mixture was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered off and concentrated. Both fractions were combined and purified by silica gel chromatography (dichloromethane/methanol gradient: from 100:0 to 10:1). This gave 12.16 g (81% of theory, purity 76%) of the target compound. the reaction solution was stirred at RT overnight The mixture was concentrated diluted with ethyl acetate The mixture was then washed with water, saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution The organic phase was dried over sodium sulphate filtered off concentrated The aqueous phase was concentrated the mixture was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution dried over sodium sulphate filtered off concentrated purified by silica gel chromatography (dichloromethane/methanol gradient: from 100:0 to 10:1)

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

Procedure: 5.0 g (47.6 mmol) of rac-1-amino-3-methoxypropan-2-ol were initially charged in THF (158 ml), and 7.36 ml (52.3 mmol) of benzyl chlorocarbonate, 24.85 ml (142.7 mmol) of N,N-diisopropyl ethyl amine and 1.16 g (9.5 mmol) of 4-dimethylaminopyridine were added. The reaction mixture was stirred at RT for 16 h. 3.7 ml (26.2 mmol) of benzyl chlorocarbonate and then 15 ml of DMF were added, and the reaction solution was stirred at RT overnight. The mixture was concentrated and diluted with ethyl acetate. The mixture was then washed with water, saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, filtered off and concentrated. The aqueous phase was concentrated, the residue was taken up in ethyl acetate, the mixture was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered off and concentrated. Both fractions were combined and purified by silica gel chromatography (dichloromethane/methanol gradient: from 100:0 to 10:1). This gave 12.16 g (81% of theory, purity 76%) of the target compound. the reaction solution was stirred at RT overnight The mixture was concentrated diluted with ethyl acetate The mixture was then washed with water, saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution The organic phase was dried over sodium sulphate filtered off concentrated The aqueous phase was concentrated the mixture was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution dried over sodium sulphate filtered off concentrated purified by silica gel chromatography (dichloromethane/methanol gradient: from 100:0 to 10:1)

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

Procedure: 19.69 g of triethylamine are added to a solution of 10.23 g of 1-amino-3- methoxy-2-propanol in 100 ml of tetrahydrofuran. After the mixture is cooled, a solution of 16.60 g of benzyloxycarbonyl chloride in 50 ml of tetrahydrofuran is added dropwise thereto for 30 minutes. The mixture is stirred at room temperature for one hour. The reaction mixture is diluted with ethyl acetate, washed with water and dried. The residue is purified by silica gel column chromatography [solvent: ethyl acetate - hexane (2:1)]. 13.2 g of 1-benzyloxycarbonylamino-3- methoxy-2-propanol are obtained as colorless oil. After the mixture is cooled washed with water dried The residue is purified by silica gel column chromatography [solvent: ethyl acetate - hexane (2:1)]

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

Procedure: 19.69 g of triethylamine are added to a solution of 10.23 g of 1-amino-3-methoxy-2-propanol in 100 ml of tetrahydrofuran. After the mixture is cooled, a solution of 16.60 g of benzyloxycarbonyl chloride in 50 ml of tetrahydrofuran is added dropwise thereto for 30 minutes. The mixture is stirred at room temperature for one hour. The reaction mixture is diluted with ethyl acetate, washed with water and dried. The residue is purified by silica gel column chromatography [solvent: ethyl acetate-hexane (2:1)]. 13.2 g of 1-benzyloxycarbonylamino-3-methoxy-2-propanol are obtained as colorless oil. ##STR24## After the mixture is cooled washed with water dried The residue is purified by silica gel column chromatography [solvent: ethyl acetate-hexane (2:1)]

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

Procedure: Twelve and six tenths (12.6) grams of 1-amino-3-methoxy-2-propanol and 16.9 grams of p-chlorobenzaldehyde were combined in 150 milliliters of benzene and heated to reflux under a modified Dean-Stark apparatus until about 2.5 milliliters of water were azeotropically removed. An additional 50 milliliters of benzene was distilled over and the mixture was cooled to room temperature and the volume was adjusted to 109.2 milliliters, so that 4 milliliters=1 gram of intermediate. Aliquots of this solution were used in subsequent reactions. heated were azeotropically removed An additional 50 milliliters of benzene was distilled over and the mixture