(3S,4R)-4-aminooxan-3-ol

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

Procedure: A mixture of the sulfone (see example 95 for preparation) (0.50 g, 1.31 mmol) and trans-4-amino-3-hydroxy-tetrahydropyran (0.23 g, 1.97 mmol) (see following ref for preparation: (a) Marquis, Robert W et al J. Med. Chem. (2001), 44(5), 725-736. (b) Gribble, Andrew D et al PCT Int. Appl. (1998), 74 pp. (c) Mochalin, V. B et al Zh. Org. Khim. (1971), 7(4), 825-8). in 2 mL of 1-methyl-2-pyrrolidinone was heated at 100° C. for 12 h. The reaction mixture was cooled, ethyl acetate (15 mL) was added and the organic solution was washed with water (3×, 15 mL), brine and then dried (MgSO4). Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3) afforded 120 mg of product (mpt. 174.9-176.3° C., MS (M+H)=419) The reaction mixture was cooled the organic solution was washed with water (3×, 15 mL), brine dried (MgSO4) Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3)

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

Procedure: A mixture of the sulfone (see example 95 for preparation) (0.50 g, 1.31 mmol) and trans-4-amino-3-hydroxy-tetrahydropyran (0.23 g, 1.97 mmol) (see following ref for preparation: (a) Marquis, Robert W et al J. Med. Chem. (2001), 44(5), 725-736. (b) Gribble, Andrew D et al PCT Int. Appl. (1998), 74 pp. (c) Mochalin, V. B et al Zh. Org. Khim. (1971), 7(4), 825-8). in 2 mL of 1-methyl-2-pyrrolidinone was heated at 100° C. for 12 h. The reaction mixture was cooled, ethyl acetate (15 mL) was added and the organic solution was washed with water (3×, 15 mL), brine and then dried (MgSO4). Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3) afforded 120 mg of product (mpt. 174.9-176.3° C., MS (M+H)=419) The reaction mixture was cooled the organic solution was washed with water (3×, 15 mL), brine dried (MgSO4) Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3)

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

Procedure: A mixture of the sulfone (see example 95 for preparation) (0.50 g, 1.31 mmol) and trans-4-amino-3-hydroxy-tetrahydropyran (0.23 g, 1.97 mmol) (see following ref for preparation: (a) Marquis, Robert W et al J. Med. Chem. (2001), 44(5), 725-736. (b) Gribble, Andrew D et al PCT Int. Appl. (1998), 74 pp. (c) Mochalin, V. B et al Zh. Org. Khim. (1971), 7(4), 825-8). in 2 mL of 1-methyl-2-pyrrolidinone was heated at 100° C. for 12 h. The reaction mixture was cooled, ethyl acetate (15 mL) was added and the organic solution was washed with water (3×, 15 mL), brine and then dried (MgSO4). Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3) afforded 120 mg of product (mpt. 174.9-176.3° C., MS (M+H)=419) The reaction mixture was cooled the organic solution was washed with water (3×, 15 mL), brine dried (MgSO4) Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3)

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

Procedure: A mixture of the sulfone (see example 95 for preparation) (0.50 g, 1.31 mmol) and trans-4-amino-3-hydroxy-tetrahydropyran (0.23 g, 1.97 mmol) (see following ref for preparation: (a) Marquis, Robert W et al J. Med. Chem. (2001), 44(5), 725-736. (b) Gribble, Andrew D et al PCT Int. Appl. (1998), 74 pp. (c) Mochalin, V. B et al Zh. Org. Khim. (1971), 7(4), 825-8). in 2 mL of 1-methyl-2-pyrrolidinone was heated at 100° C. for 12 h. The reaction mixture was cooled, ethyl acetate (15 mL) was added and the organic solution was washed with water (3×, 15 mL), brine and then dried (MgSO4). Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3) afforded 120 mg of product (mpt. 174.9-176.3° C., MS (M+H)=419) The reaction mixture was cooled the organic solution was washed with water (3×, 15 mL), brine dried (MgSO4) Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3)

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

Procedure: To a solution of 3-amino-1,5-anhydro-2,3-dideoxy-threo-pentitol (3.20 g) in ethanol (100 mL) was added 4-thioxo-1,3-thiazolidin-2-one (3.63 g), and the mixture was heated under reflux overnight. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.36 g). the mixture was heated under reflux overnight The reaction mixture was filtered the filtrate was concentrated under reduced pressure the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

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

Procedure: A mixture of the sulfone (see example 95 for preparation) (0.50 g, 1.31 mmol) and trans-4-amino-3-hydroxy-tetrahydropyran (0.23 g, 1.97 mmol) (see following ref for preparation: (a) Marquis, Robert W et al J. Med. Chem. (2001), 44(5), 725–736. (b) Gribble, Andrew D et al PCT Int. Appl. (1998), 74 pp. (c) Mochalin, V. B et al Zh. Org. Khim. (1971), 7(4), 825–8). in 2 mL of 1-methyl-2-pyrrolidinone was heated at 100° C. for 12 h. The reaction mixture was cooled, ethyl acetate (15 mL) was added and the organic solution was washed with water (3×, 15 mL), brine and then dried (MgSO4). Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3) afforded 120 mg of product (mpt. 174.9–176.3° C., MS (M+H)=419) The reaction mixture was cooled the organic solution was washed with water (3×, 15 mL), brine dried (MgSO4) Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3)

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

Procedure: A mixture of the sulfone (see example 95 for preparation) (0.50 g, 1.31 mmol) and trans-4-amino-3-hydroxy-tetrahydropyran (0.23 g, 1.97 mmol) (see following ref for preparation: (a) Marquis, Robert W et al J. Med. Chem. (2001), 44(5), 725-736. (b) Gribble, Andrew D et al PCT Int. Appl. (1998), 74 pp. (c) Mochalin, V. B et al Zh. Org. Khim. (1971), 7(4), 825-8). in 2 mL of 1-methyl-2-pyrrolidinone was heated at 100° C. for 12 h. The reaction mixture was cooled, ethyl acetate (15 mL) was added and the organic solution was washed with water (3×, 15 mL), brine and then dried (MgSO4). Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3) afforded 120 mg of product (mpt. 174.9-176.3° C., MS (M+H)=419) The reaction mixture was cooled the organic solution was washed with water (3×, 15 mL), brine dried (MgSO4) Evaporation of the solvent under reduced pressure and column chromatography (CH2Cl2/methanol—97/3)