Efficient preparation of chiral diamines via Red-Al reduction of N-Boc-protected amino acid-derived secondary amides

Tetrahedron Letters

Volumn 47, Issue 11, 2006, Pages 1717-1720

  Voight, Eric A ^a   Bodenstein, Matthew S ^a   Ikemoto, Norihiro ^a   Kress, Michael H ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID; DIAMINE; LANEPITANT; UREA;

ARTICLE; CHIRALITY; REDUCTION; SYNTHESIS;

EID: 32244448998     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.056     Document Type: Article

References (27)

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23. 4, filtered, and concentrated, giving a glassy solid. THF (1.5 mL) and toluene (3.1 mL) were added with stirring, and the mixture was cooled to <5°C. Red-Al (6.90 mL, 23.0 mmol) was added dropwise, keeping the temperature ≤20°C. The clear solution was heated to 40°C. After 14 h, the solution was cooled to <5°C and 5 N NaOH (10 mL) was added carefully, keeping the temperature <25°C. After stirring for 20 min at room temperature, toluene (30 mL) was added, the layers were separated, and the organic layer was washed with 5 N NaOH (2 × 10 mL) and concentrated. Purification by flash column chromatography (10-30% MTBE/hexanes) gave 11g (R = i-Pr, R′ = Ph, 1.11 g, 3.99 mmol, 87% yield).
24. 3): δ 155.9, 139.0, 129.2 × 2, 128.5 × 2, 126.3, 79.2, 63.3, 55.9, 50.6, 50.4, 50.1, 42.7, 38.4, 32.8, 31.0, 28.5 × 3, 27.0, 25.0, 23.1, 22.8, 15.7.
25. The stereochemical integrity of each reduction was assumed based on the analysis of compound 18 (Scheme 4).
26. 4/TMSCl: A. Giannis, and K. Sandhoff Angew. Chem. 101 1989 220
27. 2 at 2% per min with a 3 min hold at 40% MeOH; 1.5 mL/min; 200 bar; 35°C; 215 nm; retention times: (R)-18 = 16.8 min, (S)-18 = 15.5 min.