Efficient synthesis of (R)-3-amino-1,1,1-trifluoropropan-2-ol via a Dakin-West reaction followed by enantioselective reduction

Tetrahedron Asymmetry

Volumn 19, Issue 23, 2008, Pages 2648-2651

  Wei, Lulin ^a   Makowski, Teresa ^a   Martinez, Carlos ^a   Ghosh, Arun ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; 3 AMINO 1,1,1 TRIFLUOROPROPAN 2 OL; ALCOHOL; CHOLESTEROL ESTER; CHOLESTEROL ESTER TRANSFER PROTEIN INHIBITOR; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CHROMATOGRAPHY; DAKIN WEST REACTION; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 58349117440     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.12.001     Document Type: Article

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51. + (20 mg) were then charged as solids and the jacket temperature is maintained at 35 °C. The titrator (Metrohm Titrando pH autotitrator) is turned on and the reaction mixture is maintained at 6.5 by the addition of 4 M NaOH using the autotitrator. After reaction completion (∼18 h), solid KCl (2.0 g) and Celite 545 (1 g) were added to the solution followed by ethyl acetate (11 mL) and the mixture was extracted for 10 min keeping the temperature at 35 °C. The extraction was repeated two more times, and the organic layers were separated and concentrated to a pale yellow solid. The crude material was obtained in high yield (95-98% yield, based on the potency of 6) and purity (Chiral HPLC).