Asymmetric synthesis of diarylmethylamines: Preparation of selective opioid delta receptor ligands

Tetrahedron Asymmetry

Volumn 9, Issue 22, 1998, Pages 3963-3966

  Delorme, Daniel ^a,b   Berthelette, Carl ^a   Lavoie, Rico ^a   Roberts, Edward ^a  

^a Astra Research Centre Montreal   (Canada)

^b METHYLGENE INC   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DELTA OPIATE RECEPTOR; OPIATE; OXAZOLIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY; CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOMER; MASS SPECTROMETRY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032573617     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00419-4     Document Type: Article

References (28)

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14. b.
15. 3); δ: 61.58, 62.87, 66.99, 127.30, 127.44, 127.58, 127.79, 128.77, 128.90, 131.50.
16. Compound 3: HPLC (Chiracel OD, 10% i-PrOH in hexanes, 1 ml/min, λ=215 nm) >95% de.
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20. 25+2.3 (c 1.0, MeOH).
21. Compound 5: GC-MS (method 200-280, column HP-5, 1 ml/min) 92% de.
22. 5 and the following synthetic scheme: (equation presented)
23. 2:DMF 9:1 followed by the addition of diethylamine at 0°C. This procedure gave 90% yield of aldehyde 6.
24. Compound 10: GC-MS (method 200-280, column HP-5, 1 ml/min) 93% de.
25. 2).
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27. 2).
28. 2).