Development of Jacobsen Asymmetric Epoxidation and Sharpless Asymmetric Dihydroxylation Methods for the Large-Scale Preparation of a Chiral Dihydrobenzofuran Epoxide

Organic Process Research and Development

Volumn 7, Issue 6, 2003, Pages 821-827

  Siva Prasad, J ^a   Vu, Truc ^a   Totleben, Michael J ^a   Crispino, Gerard A ^a   Kacsur, David J ^a   Swaminathan, Shankar ^a   Thornton, John E ^a   Fritz, Alan ^a   Singh, Ambarish K ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLOROPERBENZOIC ACID; ALCOHOL; DICHLOROMETHANE; DIHYDROBENZOFURAN DERIVATIVE; DIHYDROBENZOFURAN EPOXIDE; EPOXIDE; OXIDE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; CRYSTALLIZATION; DISSOLUTION; ENANTIOMER; EPOXIDATION; JACOBSEN ASYMMETRIC EPOXIDATION; QUANTITATIVE ANALYSIS; SHARPLESS ASYMMETRIC DIHYDROXYLATION; SUBSTITUTION REACTION;

EID: 0347996091     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op025622e     Document Type: Article

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49. The olefin 2, available as a solution in t-BuOH containing ∼2% of MTBE was used. If MTBE is present in greater than 10% v/v, the reaction stalls.
50. The diol 5 is more soluble in EtOAc, but BuOAc affords a superior azeotropic removal of water during the subsequent concentration prior to crystallization. Lab experiments have demonstrated that when the water content of the rich organic was > 0.8% w/w, the diol crystallized in wet clumps which badly adhered to the reactor walls and agitator shaft.
51. As shown by HPLC analysis, the diol was stable in this mixture for up to 17 h at 20-25°C.
52. 4.
53. The acid wash removes the chiral ligand. The acidic aqueous phase can then be basified with NaOH, and the ligand can be extracted into toluene. See ref 15.
54. 4 or 5-10 M NaOH solution.
55. If the reaction stalls, additional charges of trimethylorthoacetate and TMSCl can be made.