The preparation of single enantiomer 2-naphthylalanine derivatives using rhodium-methyl BoPhoz-catalyzed asymmetric hydrogenation

Organic Process Research and Development

Volumn 9, Issue 4, 2005, Pages 472-478

  Boaz, Neil W ^a   Large, Shannon E ^a   Ponasik Jr , James A ^a   Moore, Mary K ^a   Barnette, Theresa ^a   Nottingham, W Dell ^a  

^a EASTMAN CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23044457042     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op050026g     Document Type: Article

References (62)

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59. The reaction time can be signficantly shortened by performing the reaction under pressure above the boiling point of the solvent (reaction times as short as 40 min have been observed using a microwave reactor at 115°C). These types of facilities were unavailable to us during scale-up.
60. Methanesulfonate 8 (8.1 mg, 0.025 mmol) was slurried in 1 mL of dichloromethane, and triethylamine (11 μL, 0.079 mmol, 3.1 equiv) was added to afford a homogeneous solution. Acetic anhydride (6 mL, 0.064 mmol, 2.5 equiv) was added and the mixture was allowed to sit for 1 h. The mixture was diluted with 3 mL of ethyl acetate, then washed with 3 M HCl (1 mL) and saturated sodium bicarbonate (1 mL). The solution of 7a thus generated was dried (magnesium sulfate) and analyzed directly by either chiral GC or HPLC to determine the ee.
61. 2O by comparing the integration of the product peak (one proton) at 4.37 ppm with the starting material peak (three protons) at 3.75 ppm to determine the conversion.
62. 2O by comparing the integration of the product peak (one proton) at 4.25 ppm with the starting material peak (one proton) at 3.55 ppm to determine the conversion.