Potassium Carbonate → tert-butyl 3-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)propanoate

HRID 400767

반응식

HRID 400767 반응식
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>C(#N)C>[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 256128tert-Butyl 3-bromopropionateHCID 101762437-Cyano-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 66795480tert-butyl 3-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)propanoate수율 94%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

7-cyano-1,2,3,4-tetrahydroisoquinoline (7 g; 44.3 mmol; 1 eq.) and potassium carbonate (10.4 g; 75.2 mmol; 1.7 eq.) were suspended in ACN (280 mL) to which was added t-butyl 3-bromopropionate (11.5 mL; 68.6 mmol; 1.05 eq.). The reaction mixture was heated to 70° C. for 24 h. Solvents were removed under vacuum and solid residue partitioned between a saturated aqueous solution of NaHCO3 and EtOAc. Organic layers was washed with brine, dried over magnesium sulfate, filtered and concentrated to afford the title compound (11.86 g; 94%) as a yellow oil. 1H NMR (DMSO-d6) δ 7.57-7.54 (m, 2H), 7.32-7.29 (m, 1H), 3.59 (s, 2H), 2.87-2.83 (t, J=5.94 Hz, 2H), 2.74-2.66 (m, 4H), 2.46-2.42 (t, J=7.01 Hz, 2H), 1.39 (s, 9H). LC/MS (Method B): 287.1 (M+H)+. HPLC (Method A) Rt 2.37 min (Purity: 96.4%).

후처리

  1. customSolvents were removed under vacuum and solid residue
  2. custompartitioned between a saturated aqueous solution of NaHCO3 and EtOAc
  3. washOrganic layers was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ad3c208b1fa444499ca38012cc4827ef
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741923B2

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