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Synlett
Volumn , Issue 13, 2009, Pages 2157-2161
Enantioselective ring expansion of prolinols: An efficient and short synthesis of 2-phenylpiperidin-3-ol derivatives and 3-hydroxypipecolic acids
Author keywords

2 Phenylpiperidin 3 ols; 3 Hydroxypipecolic acids; Aziridinium; Grignard addition; Reduction; Ring expansion
Indexed keywords

2 PHENYLPIPERIDIN 3 OL DERIVATIVE; 3 HYDROXYPIPECOLIC ACID; PIPECOLIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;
EID: 68849101596     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217568     Document Type: Article
Times cited : (34)
References (98)
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    • 3N (3 equiv), in refluxing THF for 48 h, led to the ring-expanded compounds.
    • 3N (3 equiv), in refluxing THF for 48 h, led to the ring-expanded compounds.
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    • The excellent diastereoselectivity in the DIBAL-H/Grignard sequence was probably due to catalysis of the conversion of R2 to R1 (Scheme 3) due to the presence of MgBr2 in the Grignard reagent, whereas ZnCl2 or heat was used for this purpose in Ref. 14c
    • 2 or heat was used for this purpose in Ref. 14c
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    • Ester reduction/alkylation method: DIBAL-H (1.0 M in hexane, 2.61 mL, 2.61 mmol, 1.2 equiv) was added to a solution of N-benzylproline ethyl ester (500 mg, 2.17 mmol, 1 equiv) in CH2Cl2 (10 mL) at -78°C. The resulting solution was stirred at -78°C for 30 min, followed by the addition of commercially available PhMgBr (1.0 M in THF, 6.52 mL, 6.52 mmol, 3 equiv) dropwise at -78°C. The solution was then allowed to slowly warm to r.t. overnight. Sat. aq NH4Cl (10 mL) was added to quench the reaction. Sat. sodium tartrate solution (10 mL) was added to the resulting gel. The mixture was stirred at r.t. for 30 min, then the organic layer was extracted with CH2Cl2 (3 x 15 mL, The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo to give a separable mixture of diastereomers 2b and 3b, which was purified by flash chromatography SiO2; EtOAc-PE, 8:2
    • +].
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    • General procedure for the ring expansion of pyrrolidines to piperidines: Trifluoroacetic anhydride (3-4 equiv) was added to a stirred solution of N-alkyl pyrrolidine (1 equiv) in THF under argon at r.t. and Et3N (4-7 equiv) was added. The solution was stirred and heated at 100°C for 3 h under microwave irradiation. The resulting solution was cooled to r.t. and a solution of aqueous 3.75 M NaOH was added. After stirring for 30 min, EtOAc was added and the two layers were separated. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over anhydrous MgSO4 and evaporated under reduced pressure to give the crude product. Compound 4: Chromatography (SiO2; EtOAc-PE, 7:3, Rf, 0.33 (EtOAc-PE, 7:3, ee >99% determined by supercritical fluid chromatography on Daicel Chiralpak ODH column (MeOH 5, flow rate 5 mL/min, t, 3.94 min, α]D20 -25 c
    • +].
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.