Stereoselective synthesis of 5-[(1S)-N-Boc-amino-(2S)-(3-fluorophenyl) ethyl]-dihydrofuran-2-one

Tetrahedron Letters

Volumn 45, Issue 37, 2004, Pages 6887-6890

  Li, Bryan ^a   Buzon, Richard A ^a   Chiu, Charles K F ^a   Colgan, Stephen T ^a   Jorgensen, Matthew L ^a   Kasthurikrishnan, Narasim ^a  

^a PFIZER INC   (United States)

Author keywords

Aminoketone; Organozincate; Thioester

Indexed keywords

5 [N TERT BUTYLOXYCARBONYLAMINO (3 FLUOROPHENYL)ETHYL]DIHYDROFURAN 2 ONE; ANTIVIRUS AGENT; FURAN DERIVATIVE; KETONE DERIVATIVE; PHTHALIC ANHYDRIDE; RENIN INHIBITOR; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SCREENING; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 4344693086     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.097     Document Type: Article

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35. +
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39. Chiral HPLC conditions: ChiralPak column OD 4.6 × 250 mm; mobile phase: n-hexane/isopropanol/triethylamine: 1000/20/1; flow rate: 1.5 mL/min, 40°C, 210 nm
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41. Allowing at least 30 min of good stirring with the saturated bicarbonate solution for the phthalic anhydride hydrolysis before layer separation
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43. 2 solution in THF (4 equiv, 8 mmol, 16 mL). [1-(Ethoxycyclopropyl)oxy]-trimethylsilane (8 equiv, 16 mmol, 2.81 g) was added via a syringe. The mixture was stirred at ambient temperature for 4 h, then stripped to an oil under vacuum at 25-30°C. THF (10 mL) was added. This solution was transferred to another dry and nitrogen purged 25 mL flask that contained 2 (682 mg, 2.0 mmol), phthalic anhydride (3.00 equiv; 6.0 mmol; 897 mg), and dichlorobis-(triethylphosphine)palladium(II) (0.05 equiv; 0.1 mmol; 42.8 mg) in DMAc (3.4 mL). After overnight stirring at ambient temperature, the reaction was assayed by HPLC, and showed desired product, but the reaction was incomplete (28% starting material by HPLC area). The reaction was worked up as described in method 1. The final concentrated residue was chromatographed on silica gel eluting with 20% ethyl acetate/hexanes to give 285 mg of desired product (54% yield, 192 mg of 2 was recovered). Note: the product obtained should be treated once with DarCo-G60 to purge the residual palladium in order to obtain high diastereoselectivity in the N-Selectride reduction reaction
44. 8