(2S)-2-(methoxymethyl)oxirane

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

Procedure: In a 50 mL-volumetric autoclave were added deaerated methanol (10 mL) and t-amyl alcohol (10 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-methylglycidyl ether (1.8 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (1 MPa) was introduced therein and the mixture was reacted at 40° C. for 8 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-methoxy-3-hydroxybutanoic acid methyl ester (2.7 g, 92%, >99% ee) as a colorless oil. was introduced the mixture was reacted at 40° C. for 8 hours the solvent was removed in vacuo The residue was subjected to Kugelrohr distillation

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

Procedure: In a 50 mL-volumetric autoclave were added deaerated methanol (10 mL) and t-amyl alcohol (10 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-methylglycidyl ether (1.8 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (1 MPa) was introduced therein and the mixture was reacted at 40° C. for 8 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-methoxy-3-hydroxybutanoic acid methyl ester (2.7 g, 92%, >99% ee) as a colorless oil. was introduced the mixture was reacted at 40° C. for 8 hours the solvent was removed in vacuo The residue was subjected to Kugelrohr distillation

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

Procedure: In a 50 mL-volumetric autoclave were added deaerated ethanol (10 mL) and toluene (10 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-methylglycidyl ether (1.8 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (1 MPa) was introduced therein and the mixture was reacted at 40° C. for 20 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-methoxy-3-hydroxybutanoic acid ethyl ester (3.0 g, 92%, >99% ee) as a colorless oil. was introduced the mixture was reacted at 40° C. for 20 hours the solvent was removed in vacuo The residue was subjected to Kugelrohr distillation

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

Procedure: This compound was prepared from 4-cyano-1H-imidazole-2-carboxylic acid [4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in Example 14, step (c)) according to the procedure in Example 46 step (a) using (S)-glycidyl methyl ether as the electrophile. 1H-NMR (400 MHz, CD3OD): δ 8.10 (d, J=8.3 Hz, 1H), 7.98 (s, 1H), 7.15 (dd, J=8.3, 2.1 Hz, 1H), 7.07 (d, J=2.1 Hz, 1H), 5.73 (m, 1H), 3.91 (m, 1H), 3.36 (s, 3H), 2.80 (dd, J=13.7, 5.7 Hz, 1H), 2.69 (dd, J=13.7, 7.5 Hz, 1H), 2.31 (m, 2H), 2.07 (m, 2H), 1.58 (t, J=6.3 Hz, 2H), 1.07 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C23H28N4O3, 409.2 (M+H). found 409.1.

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (S)-methyl glycidyl ether (10 g) and benzylamine (3.62 g) in methanol (50 ml) was stirred at 55° C. for 2 hours. To the mixture was added (S)-methyl glycidyl ether (1 g), and the mixture was stirred at 55° C. for 2 hours, and then evaporated under reduced pressure. Toluene was added to the residue and evaporated under reduced pressure to give (2S)-1-[N-benzyl-N-[(2S)-2-hydroxy-3-methoxypropyl]amino]-3-methoxypropan-2-ol (8.84 g) as a pale yellow oil. evaporated under reduced pressure Toluene was added to the residue evaporated under reduced pressure

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

Procedure: This compound was prepared from 4-cyano-1H-imidazole-2-carboxylic acid [4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in Example 14, step (c)) according to the procedure in Example 46 step (a) using (S)-glycidyl methyl ether as the electrophile. 1H-NMR (400 MHz, CD3OD): δ 8.10 (d, J=8.3 Hz, 1H), 7.98 (s, 1H), 7.15 (dd, J=8.3, 2.1 Hz, 1H), 7.07 (d, J=2.1 Hz, 1H), 5.73 (m, 1H), 3.91 (m, 1H), 3.36 (s, 3H), 2.80 (dd, J=13.7, 5.7 Hz, 1H), 2.69 (dd, J=13.7, 7.5 Hz, 1H), 2.31 (m, 2H), 2.07 (m, 2H), 1.58 (t, J=6.3 Hz, 2H), 1.07 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C23H28N4O3, 409.2 (M+H). found 409.1.

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

Procedure: In a 50 mL-volumetric autoclave were added deaerated methanol (10 mL) and t-amyl alcohol (10 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-methylglycidyl ether (1.8 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (1 MPa) was introduced therein and the mixture was reacted at 40° C. for 8 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-methoxy-3-hydroxybutanoic acid methyl ester (2.7 g, 92%, >99% ee) as a colorless oil. was introduced the mixture was reacted at 40° C. for 8 hours the solvent was removed in vacuo The residue was subjected to Kugelrohr distillation

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

Procedure: In a 50 mL-volumetric autoclave were added deaerated ethanol (10 mL) and toluene (10 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-methylglycidyl ether (1.8 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (1 MPa) was introduced therein and the mixture was reacted at 40° C. for 20 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-methoxy-3-hydroxybutanoic acid ethyl ester (3.0 g, 92%, >99% ee) as a colorless oil. was introduced the mixture was reacted at 40° C. for 20 hours the solvent was removed in vacuo The residue was subjected to Kugelrohr distillation