CID 71433566 → N-((1S,2R)-1-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide

HRID 587804Notizen

Reaktionsgleichung

C[C@H](P)[C]1[C](P(C2C3C(=CC=CC=3)C=CC=2)C2C3C(=CC=CC=3)C=CC=2)[CH][CH][CH]1.[CH2:30]([C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([O:47][CH3:48])[CH:45]=2)[CH2:40][CH2:39][C:38]=1[NH:49][C:50](=[O:53])[CH2:51][CH3:52])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[H][H]>[Rh+].ClC1CCCCC=CC=1.CO>[CH2:30]([C@H:37]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([O:47][CH3:48])[CH:45]=2)[CH2:40][CH2:39][C@H:38]1[NH:49][C:50](=[O:53])[CH2:51][CH3:52])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Chlorocyclooctadiene rhodium(I) dimer (0.072 g, 0.292 mmol), Josiphos SL-J216-1 (0.197 g, 0.307 mmol), and N-(1-benzyl-7-methoxy-3,4-dihydronaphthalen-2-yl)propionamide (19.75 g, 61.4 mmol) were combined in a 500 ml SS pressure bottle, and the vessel was inerted with argon. Degassed methanol (200 ml) was added, the vessel was again inerted, then the mixture was stirred under 20 psig of argon at 50° C. for 20 min. The vessel was then pressurized with 60 psig of hydrogen and stirred at 55° C. for 14 hrs. HPLC analysis (YIYINADH.M, s.m. 9.08 min. with a 1.5 PA % impurity at 12.14 min., product enantiomers 9.45 and 13.41 min.) indicated 100% conversion and 95.6% ee. Crystallization from MeOH afforded the title compound (yield: 15%; ee: 99.5%).

Aufarbeitung

stirringstirred at 55° C. for 14 hrs
wait9.08 min. with a 1.5 PA % impurity at 12.14 min.
customproduct enantiomers 9.45 and 13.41 min.
customCrystallization from MeOH

Quellen und Nachweise

ORD-Eintrag: ord-454793aed9f54226b5ce17a7585c34fb
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09227901B2

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