Efficient synthesis of 1-heterocyclic-3-aminopyrrolidinones

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1141-1145

  Bell, Ian M ^a   Beshore, Douglas C ^a   Gallicchio, Steven N ^a   Williams, Theresa M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

3 aminopyrrolidinones; Cyclization; Mitsunobu reaction; Nitrogen heterocycles

Indexed keywords

GAMMA LACTAM DERIVATIVE; HETEROCYCLIC COMPOUND; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; DEHYDRATION; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034685246     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02282-0     Document Type: Article

References (19)

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18. Synthesized by EDC/HOBT-mediated cyclization of (S)-N-(tert-butoxycarbonyl)homoserine.
19. 3) δ 8.38-8.34 (2H, m), 7.70 (1H, ddd, J=8.4, 7.3, 1.8 Hz), 7.59-7.56 (2H, m), 7.44-7.38 (3H, m), 7.32 (1H, br d, J=5.5 Hz), 7.07 (1H, ddd, J=7.2, 4.9, 0.9 Hz), 4.68 (1H, ddd, J=11.4, 8.4, 6.0 Hz), 4.29 (1H, ddd, J=10.3, 9.1, 0.9 Hz), 3.87 (1H, td, J=11.0, 6.6 Hz), 3.40 (3H, q, J=1.3 Hz), 2.81 (1H, m), 1.94 (1H, m). The (S,R)-diastereomer was also synthesized (by the same method but using the (S)-Mosher's acid chloride) for comparison purposes.