(R)-3-ISOPROPYLMORPHOLINE,

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

Procedure: To ice-cold tetrahydrofuran (8.0 mL) was added lithium aluminum hydride (1.0 M solution in tetrahydrofuran, 23.0 mL, 23.0 mmol). Once the addition was complete, a solution of (R)-5-isopropylmorpholin-3-one (1.7 g, 12.0 mmol) in tetrahydrofuran (8 mL) was added dropwise over 20 min. Once the addition was completed, the ice bath was removed and the reaction mixture stirred at reflux for 20 h. The reaction was cooled in an ice-bath and to this was slowly added water (1.0 mL), then a 15% solution of sodium hydroxide (1.0 mL), and then water (1.0 mL). The resulting mixture was stirred at room temperature for 1.5 h and then filtered washing the solid with ethyl acetate (50 mL). The filtrate was concentrated at room temperature under reduced pressure to provide (R)-3-isopropylmorpholine (1.4 g, 93%) as a light yellow oil. 1H NMR consistent. Once the addition Once the addition the ice bath was removed at reflux for 20 h The reaction was cooled in an ice-bath The resulting mixture was stirred at room temperature for 1.5 h filtered washing the solid with ethyl acetate (50 mL) The filtrate was concentrated at room temperature under reduced pressure

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

Procedure: To ice-cold tetrahydrofuran (8.0 mL) was added lithium aluminum hydride (1.0 M solution in tetrahydrofuran, 23.0 mL, 23.0 mmol). Once the addition was complete, a solution of (R)-5-isopropylmorpholin-3-one (1.7 g, 12.0 mmol) in tetrahydrofuran (8 mL) was added dropwise over 20 min. Once the addition was completed, the ice bath was removed and the reaction mixture stirred at reflux for 20 h. The reaction was cooled in an ice-bath and to this was slowly added water (1.0 mL), then a 15% solution of sodium hydroxide (1.0 mL), and then water (1.0 mL). The resulting mixture was stirred at room temperature for 1.5 h and then filtered washing the solid with ethyl acetate (50 mL). The filtrate was concentrated at room temperature under reduced pressure to provide (R)-3-isopropylmorpholine (1.4 g, 93%) as a light yellow oil. 1H NMR consistent. Once the addition Once the addition the ice bath was removed at reflux for 20 h The reaction was cooled in an ice-bath The resulting mixture was stirred at room temperature for 1.5 h filtered washing the solid with ethyl acetate (50 mL) The filtrate was concentrated at room temperature under reduced pressure

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

Procedure: To ice-cold tetrahydrofuran (8.0 mL) was added lithium aluminum hydride (1.0 M solution in tetrahydrofuran, 23.0 mL, 23.0 mmol). Once the addition was complete, a solution of (R)-5-isopropylmorpholin-3-one (1.7 g, 12.0 mmol) in tetrahydrofuran (8 mL) was added dropwise over 20 min. Once the addition was completed, the ice bath was removed and the reaction mixture stirred at reflux for 20 h. The reaction was cooled in an ice-bath and to this was slowly added water (1.0 mL), then a 15% solution of sodium hydroxide (1.0 mL), and then water (1.0 mL). The resulting mixture was stirred at room temperature for 1.5 h and then filtered washing the solid with ethyl acetate (50 mL). The filtrate was concentrated at room temperature under reduced pressure to provide (R)-3-isopropylmorpholine (1.4 g, 93%) as a light yellow oil. 1H NMR consistent. Once the addition Once the addition the ice bath was removed at reflux for 20 h The reaction was cooled in an ice-bath The resulting mixture was stirred at room temperature for 1.5 h filtered washing the solid with ethyl acetate (50 mL) The filtrate was concentrated at room temperature under reduced pressure

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

Procedure: To ice-cold tetrahydrofuran (8.0 mL) was added lithium aluminum hydride (1.0 M solution in tetrahydrofuran, 23.0 mL, 23.0 mmol). Once the addition was complete, a solution of (R)-5-isopropylmorpholin-3-one (1.7 g, 12.0 mmol) in tetrahydrofuran (8 mL) was added dropwise over 20 min. Once the addition was completed, the ice bath was removed and the reaction mixture stirred at reflux for 20 h. The reaction was cooled in an ice-bath and to this was slowly added water (1.0 mL), then a 15% solution of sodium hydroxide (1.0 mL), and then water (1.0 mL). The resulting mixture was stirred at room temperature for 1.5 h and then filtered washing the solid with ethyl acetate (50 mL). The filtrate was concentrated at room temperature under reduced pressure to provide (R)-3-isopropylmorpholine (1.4 g, 93%) as a light yellow oil. 1H NMR consistent. Once the addition Once the addition the ice bath was removed at reflux for 20 h The reaction was cooled in an ice-bath The resulting mixture was stirred at room temperature for 1.5 h filtered washing the solid with ethyl acetate (50 mL) The filtrate was concentrated at room temperature under reduced pressure