Dicyclohexylcarbodiimide → 1,2,3,4-Tetrahydro-6-methoxy-N-3-(2-thienyl)propionylisoquinoline

HRID 1088695ノート

反応式

HRID 1088695 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.O.OC1C2N=NNC=2C=CC=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][CH2:30][C:31](O)=[O:32].C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:31](=[O:32])[CH2:30][CH2:29][C:25]1[S:24][CH:28]=[CH:27][CH:26]=1)[CH2:7][CH2:6]2

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 7031693-(2-Thienyl)propanoic acidHCID 178526939HCID 178526939、化合物

生成物 1

HCID 157186901,2,3,4-Tetrahydro-6-methoxy-N-3-(2-thienyl)propionylisoquinoline収率 74.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1,2,3,4-tetrahydro-6-methoxyisoquinoline (3.29 g), hydroxybenzotriazole monohydrate (5.72 g) and 3-(2-thienyl)propanoic acid (3.31 g) in 280 ml of dry tetrahydrofuran (THF) at 0° C. was added DCC (4.37 g) in one portion. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was filtered and concentrated. The residue was taken up into 200 ml of ethyl acetate (EtOAc) refiltered, washed with 5% aq. HCl (50 ml), 5% aq. NaCl (50 ml), 10% aq. KOH (50 ml), dried (MgSO4), filtered, and concentrated. Chromatography on silica gel (elution with 20% EtOAc:hexanes) afforded 4.54 g of the desired product.

後処理

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. washwashed with 5% aq. HCl (50 ml), 5% aq. NaCl (50 ml), 10% aq. KOH (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3e5072f731db4fcb96a87b0bdc848440
出典データセット
uspto-grants-1990_10
特許番号
US04963563

反応ノート

読み込み中…