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

HRID 587804노트

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HRID 587804 반응식
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

참가 물질

6

반응물 3

HCID 71433566CID 71433566HCID 86707884HCID 86707884, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 72946494N-((1S,2R)-1-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide수율 15%

시약·촉매·용매 2

HCID 178478078HCID 178478078, 화합물촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-454793aed9f54226b5ce17a7585c34fb
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227901B2

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