(1R,2R)-cyclohexane-1,2-diamine;hydrochloride

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

Procedure: To a 500 mL flask was charged with (1R,2R)-1,2-diaminocyclohexane monohydrochloride salt (1.51 g, 10 mmol), activated 4 A molecular sieve (4.0 g), anhydrous methanol (40 mL) and ethanol (40 mL). 3,5-Di-t-butyl-2-hydroxybenzaldehyde (2.34 g, 10 mmol) was added in one portion and the reaction mixture was stirred at rt for 4 h. TLC showed that all the aldehyde was consumed. A solution of 3-(4′-vinylphenyl)-5-t-butyl-2-hydroxybenzaldehyde (2.74 g, 10 mmol) in dichloromethane (80 mL) was added to reaction system, followed by the addition of triethylamine (2.8 mL, 20 mmol) in a dropwise fashion. After the reaction mixture was stirred at rt for additional 4 h, all the solvents were removed by rotovap. The residue was dissolved in dichloromethane (100 mL), washed with aqueous hydrochloric acid (1 M, 50 mL) and water (2×50 mL), and dried with magnesium sulfate. The desired compound 1 (5.05 g, 85.2%) was isolated by flash chromatography of the crude product with 1/50 ether/hexanes. was consumed After the reaction mixture was stirred at rt for additional 4 h all the solvents were removed by rotovap The residue was dissolved in dichloromethane (100 mL) washed with aqueous hydrochloric acid (1 M, 50 mL) and water (2×50 mL) dried with magnesium sulfate

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

Procedure: To a 500 mL flask was charged with (1R,2R)-1,2-diaminocyclohexane monohydrochloride salt (1.51 g, 10 mmol), activated 4 A molecular sieve (4.0 g), anhydrous methanol (40 mL) and ethanol (40 mL). 3,5-Di-t-butyl-2-hydroxybenzaldehyde (2.34 g, 10 mmol) was added in one portion and the reaction mixture was stirred at rt for 4 h. TLC showed that all the aldehyde was consumed. A solution of 3-(4′-vinylphenyl)-5-t-butyl-2-hydroxybenzaldehyde (2.74 g, 10 mmol) in dichloromethane (80 mL) was added to reaction system, followed by the addition of triethylamine (2.8 mL, 20 mmol) in a dropwise fashion. After the reaction mixture was stirred at rt for additional 4 h, all the solvents were removed by rotovap. The residue was dissolved in dichloromethane (100 mL), washed with aqueous hydrochloric acid (1 M, 50 mL) and water (2×50 mL), and dried with magnesium sulfate. The desired compound 1 (5.05 g, 85.2%) was isolated by flash chromatography of the crude product with 1/50 ether/hexanes. was consumed After the reaction mixture was stirred at rt for additional 4 h all the solvents were removed by rotovap The residue was dissolved in dichloromethane (100 mL) washed with aqueous hydrochloric acid (1 M, 50 mL) and water (2×50 mL) dried with magnesium sulfate

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

Procedure: To a 500 mL flask was charged with (1R,2R)-1,2-diaminocyclohexane monohydrochloride salt (1.51 g, 10 mmol), activated 4 A molecular sieve (4.0 g), anhydrous methanol (40 mL) and ethanol (40 mL). 3,5-Di-t-butyl-2-hydroxybenzaldehyde (2.34 g, 10 mmol) was added in one portion and the reaction mixture was stirred at rt for 4 h. TLC showed that all the aldehyde was consumed. A solution of 3-(4′-vinylphenyl)-5-t-butyl-2-hydroxybenzaldehyde (2.74 g, 10 mmol) in dichloromethane (80 mL) was added to reaction system, followed by the addition of triethylamine (2.8 mL, 20 mmol) in a dropwise fashion. After the reaction mixture was stirred at rt for additional 4 h, all the solvents were removed by rotovap. The residue was dissolved in dichloromethane (100 mL), washed with aqueous hydrochloric acid (1 M, 50 mL) and water (2×50 mL), and dried with magnesium sulfate. The desired compound 1 (5.05 g, 85.2%) was isolated by flash chromatography of the crude product with 1/50 ether/hexanes. was consumed After the reaction mixture was stirred at rt for additional 4 h all the solvents were removed by rotovap The residue was dissolved in dichloromethane (100 mL) washed with aqueous hydrochloric acid (1 M, 50 mL) and water (2×50 mL) dried with magnesium sulfate