Water → 2-tert-butyl 3-methyl (3S)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2,3-dicarboxylate

HRID 1984827노트

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HRID 1984827 반응식
[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18]([OH:20])=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:21])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].IC.[CH:24](N(C(C)C)CC)(C)C.O>CN(C=O)C>[CH3:24][O:19][C:18]([C@@H:17]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:21])=[CH:13][CH:14]=2)[CH2:9][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:20]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 6712312(3S)-2-((tert-butoxy)carbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

생성물 1

HCID 213113062-tert-butyl 3-methyl (3S)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2,3-dicarboxylate수율 73.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (3S)-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester (1.47 g, 5.0 mmol) in dry DMF (25 mL) at ambient temperature, was added iodomethane (1.2 eq., 6.0 mmol, 0.37 mL) and diisopropylethylamine (1.5 eq. 7.5 mmol, 1.31 mL) in succession, and the reaction mixture was stirred at rt for 3-4 hours, at which point LC/MS analysis showed the presence of product The reaction mixture was poured into 50 mL of water and extracted with DCM (3×50 mL) and the combined DCM extracts were washed with water (3×50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography on silica (20-30% ethyl acetate in hexanes) to afford (3S)-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester (1.13 g).

후처리

  1. extractionextracted with DCM (3×50 mL)
  2. washthe combined DCM extracts were washed with water (3×50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography on silica (20-30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-4917a3992110405b8245a0be638895f2
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544699B2

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