Benzyl chloroformate → Benzyl 7-nitro-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

HRID 1524292노트

반응식

HRID 1524292 반응식
Cl.[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].C([O-])([O-])=O.[K+].[K+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>CCOC(C)=O.O>[CH2:25]([O:24][C:22]([N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[CH2:12]1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

생성물 1

HCID 53419203Benzyl 7-nitro-1,2,3,4-tetrahydroisoquinoline-2-carboxylate수율 91.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (11.0 g, 51.25 mmol) in EtOAc (150 mL) at 0° C. in an ice bath add a solution of K2CO3 (15.65 g, 113.25 mmol) in water (150 mL) followed by benzyl chloroformate (8.37 mL, 56.37 mmol) and vigorously stir the reaction at room temperature for 24 h. Separate the layers and extract the aqeuous with more EtOAc (150 mL). Wash the organics with sat. NaHCO3 (200 mL), sat. NH4Cl (200 mL) and water (200 mL), then dry (Na2SO4). Concentrate in vacuo to give 14.70 g of 7-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester as an oil which partially crystallizes.

후처리

  1. customthe reaction at room temperature for 24 h
  2. customSeparate the layers
  3. extractionextract the aqeuous with more EtOAc (150 mL)
  4. washWash the organics with sat. NaHCO3 (200 mL), sat. NH4Cl (200 mL) and water (200 mL)
  5. dry with materialdry (Na2SO4)
  6. concentrationConcentrate in vacuo

출처 및 근거

ORD 기록
ord-3ae326eec657426ebaa0390190a2c4ad
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079880B2

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