Ethyl Acetate → HCID 67980521, 화합물

HRID 1622305노트

반응식

HRID 1622305 반응식
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:3]2[CH2:4][CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=3)[CH2:2]2)=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 42614607Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride

생성물 1

HCID 67980521HCID 67980521, 화합물수율 104.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride (500.0 mg, 2.00 mmol) in DMF (17.0 mL) was added 4-bromobenzylbromide (604 mg, 2.42 mmol) and K2CO3 (910 mg, 6.59 mmol). The resulting mixture was stirred overnight at rt. EtOAc and water were added, and the phases were separated. The organic phase was dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography (SiO2, 0-40% EtOAc in hexane) to give methyl 2-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (753 mg, 100%). LC-MS: (FA) ES+ 361; 1H NMR (300 MHz, CDCl3) δ 7.86-7.70 (m, 2H), 7.46 (dd, J=8.7, 2.1 Hz, 2H), 7.36-7.21 (m, 2H), 7.04 (d, J=8.0 Hz, 1H), 3.89 (d, J=3.8 Hz, 3H), 3.64 (s, 4H), 2.93 (t, J=5.8 Hz, 2H), 2.83-2.64 (m, 2H).

후처리

  1. customthe phases were separated
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography (SiO2, 0-40% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-15956912804947f5a3d512b5a398d003
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778931B2

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