Reductive ring opening of 2-azetidinones promoted by sodium borohydride

Tetrahedron Letters

Volumn 47, Issue 13, 2006, Pages 2209-2211

  Del Buttero, Paola ^a   Molteni, Giorgio ^a   Roncoroni, Maurizio ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; 2 PROPANOL; SODIUM BOROHYDRIDE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CORRELATION ANALYSIS; ENERGY; REDUCTION; RING OPENING; SUBSTITUTION REACTION;

EID: 33344478127     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.103     Document Type: Article

References (21)

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16. For a typical run: A suspension of 3 or 4 (0.87 mmol) in isopropanol (11 mL) was treated with sodium borohydride (0.16 g, 4.3 mmol) in water (2 mL) and then stirred under nitrogen for 20 h. The crude was partly evaporated under reduced pressure and taken up with dichloromethane (40 mL). The organic layer was washed with water to neutrality, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel column giving open-chain products 5 or 7.
17. 3 solutions. Compound 5a: δ 3.75 (3H, s), 3.80 (1H, dd, J 11.8, 4.2), 3.95 (1H, dd, J 11.8, 4.8), 4.5-4.6 (1H, m), 4.75 (1H, d, J 4.9), 6.6-7.5 (14H, m). Compound 5b: δ 2.53 (3H, s), 3.70 (3H, s), 3.80 (1H, dd, J 11.6, 4.4), 3.95 (1H, dd, J 11.6, 5.4), 4.4-4.5 (1H, m), 4.96 (1H, d, J 4.0), 6.5-7.4 (13H, m). Compound 5c: δ 3.75 (3H, s), 3.80 (1H, dd, J 11.6, 4.2), 3.95 (1H, dd, J 11.6, 5.2), 4.5-4.6 (1H, m), 4.97 (1H, d, J 4.3), 6.6-7.5 (13H, m). Compound 5d: δ 3.70 (3H, s), 4.0-4.1 (1H, m), 4.8-4.9 (1H, m), 5.5-5.6 (1H, m), 4.97 (1H, d, J 4.3), 6.5-7.9 (13H, m).
18. 3 solutions. Compound 7a: 3.60 (1H, dd, J 10.7, 6.0), 3.70 (3H, s), 3.75 (1H, dd, J 10.7, 3.7), 3.9-4.0 (1H, m), 4.42 (1H, d, J 6.5), 6.5-7.3 (9H, m). Compound 7b: 2.42 (3H, s), 3.60 (1H, dd, J 11.4, 6.0), 3.70 (3H, s), 3.75 (1H, dd, J 11.4, 3.7), 3.9-4.0 (1H, m), 4.70 (1H, d, J 6.0), 6.5-7.4 (8H, m). Compound 7c: 3.60 (1H, dd, J 10.7, 5.2), 3.70 (3H, s), 3.8-4.0 (2H, m), 4.70 (1H, d, J 6.6), 6.7-7.3 (8H, m). Compound 7d: δ 3.70 (3H, s), 3.8-4.1 (3H, m), 5.35 (1H, d, J 5.8), 6.5-7.9 (8H, m).
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