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

HRID 1088695노트

반응식

HRID 1088695 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3e5072f731db4fcb96a87b0bdc848440
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963563

반응 노트

불러오는 중…