tert-Butanol → Tert-butyl [1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinolin-5-yl]carbamate

HRID 577517노트

반응식

HRID 577517 반응식
[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([O:12][CH:13]([CH3:15])[CH3:14])[CH:8]=[C:7](C(O)=O)[C:6]=2[CH2:5][CH2:4][NH:3]1.C1N=CN([C:24]([N:26]2C=NC=C2)=[O:25])C=1.[C:31]([OH:35])([CH3:34])([CH3:33])[CH3:32]>O1CCOCC1>[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([NH:26][C:24](=[O:25])[O:35][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:8]=[C:9]([O:12][CH:13]([CH3:14])[CH3:15])[CH:10]=2)[CH2:5][CH2:4][NH:3]1

참가 물질

5

반응물 3

HCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 867237431-Oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid

생성물 1

HCID 86723744Tert-butyl [1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinolin-5-yl]carbamate수율 42%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a suspension of 1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid (77a, 1.76 g, 7.06 mmol) in anhydrous dioxane (100 mL) was added CDI (1.43 g, 8.83 mmol). The resulting mixture was stirred at room temperature for 30 minutes, then stirred at 100° C. for 30 minutes. After cooling down to room temperature, TMSA (1.50 mL, 10.8 mmol) was added. After stirring the reaction mixture for 2 hours, t-butanol (25.0 mL) was added. The resulting mixture was stirred at 100° C. overnight. After cooling to room temperature and concentrating under vacuum, the resulting residue was purified by column chromatography (0-100% EtOAc/heptanes) to give tert-butyl [1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinolin-5-yl]carbamate (77b, 958 mg, 42%) as a solid.

후처리

  1. stirringstirred at 100° C. for 30 minutes
  2. temperatureAfter cooling down to room temperature
  3. additionTMSA (1.50 mL, 10.8 mmol) was added
  4. stirringAfter stirring the reaction mixture for 2 hours
  5. stirringThe resulting mixture was stirred at 100° C. overnight
  6. temperatureAfter cooling to room temperature
  7. concentrationconcentrating under vacuum
  8. customthe resulting residue was purified by column chromatography (0-100% EtOAc/heptanes)

출처 및 근거

ORD 기록
ord-5ba9e2ece35e4d469895539e52347839
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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