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

HRID 587804ノート

反応式

HRID 587804 の反応式
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

参加物

6

反応物 3

HCID 71433566CID 71433566HCID 86707884HCID 86707884、化合物HCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 178478078HCID 178478078、化合物触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-454793aed9f54226b5ce17a7585c34fb
出典データセット
uspto-grants-2016_01
特許番号
US09227901B2

反応ノート

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