2-methyloctan-4-one

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Benzylamine (3.1 ml, 28 mmol) was added to a stirred mixture of 2-methyloctan-4-one (4.0 g, 28 mmol) and 3 Å molecular sieves in dry methanol (40 ml) under argon. The mixture was stirred at room temperature overnight. Sodium cyanoborohydride (1.77 g, 28 mmol) was added and the mixture stirred overnight. Stirring was stopped and the solution was decanted, from the molecular sieves, into saturated aqueous ammonium chloride. The mixture was filtered, concentrated, ethyl acetate added and the mixtures washed with water. The organics were dried over anhydrous magnesium sulphate, filtered and concentrated to give a yellow oil. Chromatography (silica: 1% triethylamine and 10% ethylacetate in hexane) gave N-benzyl-2-methyl-4-aminooctane (3.0 g, 46%) as a yellow oil. the mixture stirred overnight Stirring the solution was decanted, from the molecular sieves, into saturated aqueous ammonium chloride The mixture was filtered concentrated ethyl acetate added the mixtures washed with water The organics were dried over anhydrous magnesium sulphate filtered concentrated to give a yellow oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-methyloctan-4-one (6.3 g, 44 mmol), sodium cyanoborohydride (3.0 g, 48 mmol), ammonium acetate (33.9 g, 0.44 mol) and 3 Å molecular sieves in dry methanol (50 ml) was stirred overnight at room temperature under argon. The solvent was removed under reduced pressure and the residue taken up in chloroform (100 ml), filtered through a pad of celite and concentrated to give 2-methyl-4-aminooctane (1.6 g, 25%) as a yellow oil. The solvent was removed under reduced pressure filtered through a pad of celite concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of oxalyl chloride (4.2 ml, 49 mmol) in dry DCM (200 ml) was cooled to -78° C. under argon. Dimethylsulphoxide (6.9 ml, 98 mmol) was added slowly and the mixture stirred for 5 min. 2-Methyloctan-4-ol (6.4 g, 44 mmol) was added and the mixture stirred for 20 min. Triethylamine (30.7 ml, 0.22 ml) was added and after 5 min. the mixture was allowed to warm up to room temperature. Water (100 ml) was added, the organic layer separated and the aqueous layer extracted with DCM. The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and concentrated to give 2-methyloctan-4-one (5.0 g, 79%) as a waxy oil. the mixture stirred for 20 min the organic layer separated the aqueous layer extracted with DCM The combined organic extracts were dried over anhydrous magnesium sulphate filtered concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Benzylamine (3.1 ml, 28 mmol) was added to a stirred mixture of 2-methyloctan-4-one (4.0 g, 28 mmol) and 3A molecular sieves in dry, methanol (40 ml) under argon. The mixture was stirred at room temperature overnight. Sodium cyanoborohydride (1.77 g, 28 mmol) was added and the mixture stirred overnight. Stirring was stopped and the solution was decanted, from the molecular sieves, into saturated aqueous ammonium chloride. The mixture was filtered, concentrated, ethyl acetate added and the mixture washed with water. The organics were dried over anhydrous magnesium sulphate, filtered and concentrated to give a yellow oil. Chromatography (silica: 1% triethylamine and 10% ethylacetate in hexane) gave N-benzyl -2-methyl-4-aminooctane (3.0 g, 46%) as a yellow oil. in dry the mixture stirred overnight Stirring the solution was decanted, from the molecular sieves, into saturated aqueous ammonium chloride The mixture was filtered concentrated ethyl acetate added the mixture washed with water The organics were dried over anhydrous magnesium sulphate filtered concentrated to give a yellow oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-methyloctan-4-one (6.3 g, 44 mmol), sodium cyanoborohydride (3.0 g, 48 mmol), ammonium acetate (33.9 g, 0.44 mol) and 3Å molecular sieves in dry methanol (50 ml) was stirred overnight at room temperature under argon. The solvent was removed under reduced pressure and the residue taken up in chloroform (100 ml), filtered through a pad of celite and concentrated to give 2-methyl-4-aminooctane (1.6 g, 25%) as a yellow oil. The solvent was removed under reduced pressure filtered through a pad of celite concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of oxalyl chloride (4.2 ml, 49 mmol) in dry DCM (200 ml) was cooled to -78° C. under argon. Dimethylsulphoxide (6.9 ml, 98 mmol) was added slowly and the mixture stirred for 5 min. 2-Methyloctan-4-ol (6.4 g, 44 mmol) was added and the mixture stirred for 20 min. Triethylamine (30.7 ml, 0.22 mol) was added and after 5 min. the mixture was allowed to warm up to room temperature. Water (100 ml) was added, the organic layer separated and the aqueous layer extracted with DCM. The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and concentrated to give 2-methyloctan-4-one (5.0 g, 79%) as a waxy oil. the mixture stirred for 20 min the organic layer separated the aqueous layer extracted with DCM The combined organic extracts were dried over anhydrous magnesium sulphate filtered concentrated