Stannous chloride dihydrate → Benzyl 5-aminoisoindoline-2-carboxylate

HRID 604628노트

반응식

HRID 604628 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:7]2)([O-])=O.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:7]2

참가 물질

5

반응물 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 67057710benzyl 5-nitro-1,3-dihydro-2H-isoindole-2-carboxylate

생성물 1

HCID 67057746Benzyl 5-aminoisoindoline-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of benzyl 5-nitro-1,3-dihydro-2H-isoindole-2-carboxylate (1.34 g, 4.49 mmol) in DMF (30 mL) was added SnCl2.2H2O (5.1 g, 22.5 mmol) as a powder. The mixture was stirred overnight. The reaction mixture was adjusted to basic pH with sat. aq. NaHCO3. The white precipitate formed was extracted with EtOAc (3×150 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to provide benzyl 5-amino-1,3-dihydro-2H-isoindole-2-carboxylate. LCMS calc.=269.1; found=268.9 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.46-7.34 (m, 5H); 7.12-6.93 (2 d, J=8.1, 1H); 6.66-6.53 (m, 2H); 5.25 (s, 2H); 4.69 (t, J=9.8 Hz, 4H); 3.71 (br s, 2H).

후처리

  1. customThe white precipitate formed
  2. extractionwas extracted with EtOAc (3×150 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-1d158f72af974237be62516f4e898808
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

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