CID 71433830 → N-((1R,2S)-1-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidin-2-one

HRID 587803ノート

反応式

HRID 587803 の反応式
C[C@@H](PC)[C]1[C](P(C2C3C(=CC=CC=3)C=CC=2)C2C3C(=CC=CC=3)C=CC=2)[CH][CH][CH]1.[CH2:31]([C:38]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([O:48][CH3:49])[CH:46]=2)[CH2:41][CH2:40][C:39]=1[N:50]1[CH2:54][CH2:53][CH2:52][C:51]1=[O:55])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[H][H]>[Rh+].ClC1CCCCC=CC=1.CO>[CH2:31]([C@@H:38]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([O:48][CH3:49])[CH:46]=2)[CH2:41][CH2:40][C@@H:39]1[N:50]1[CH2:54][CH2:53][CH2:52][C:51]1=[O:55])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

参加物

6

反応物 3

HCID 71433830CID 71433830HCID 86707889N-(1-benzyl-7-methoxy-3,4-dihydronaphthalen-2-yl)pyrrolidin-2-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 72946493N-((1R,2S)-1-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidin-2-one収率 82.5%

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 (3.70 mg, 15.0 μmol of Rh), Josiphos SL-J216-2 (10.16 mg, 16.0 μmol), and N-(1-benzyl-7-methoxy-3,4-dihydronaphthalen-2-yl)pyrrolidin-2-one (500.8 mg, 1.50 mmol) were combined in a glass-lined metal reactor, and the vessel was inerted with argon. Degassed methanol (5.0 ml) was added, and the mixture was agitated under 20 psi of argon at 50° C. for 20 min. The vessel was pressurized with 90 psig of hydrogen and stirred at 100° C. for 45 hrs. HPLC analysis indicated 99.8% conversion and 90.7% ee. The mixture was concentrated and diluted with water to yield 415 mg (yield: 82%) of the title compound.

後処理

  1. stirringstirred at 100° C. for 45 hrs
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water

出典と根拠

ORDレコード
ord-2a504da920704bf8b22cc262159a750e
出典データセット
uspto-grants-2016_01
特許番号
US09227901B2

反応ノート

読み込み中…