N-Formylmorpholine → Tert-butyl 5-formyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

HRID 8725

반응식

HRID 8725 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2Br)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[CH:24](N1CCOCC1)=[O:25].[Cl-].[NH4+]>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH:24]=[O:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 20417N-FormylmorpholineHCID 25517Ammonium ChlorideHCID 18315369tert-Butyl 5-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 22335239Tert-butyl 5-formyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate수율 13.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 5-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 19a (3.87 g, 12.39 mmol) in diethyl ether (60 mL) was cooled to −100° C. A solution of 1.7 M tert-butyllithium in hexanes (16.04 mL, 27.27 mmol) was added dropwise. After the addition, stirring was continued for 30 min to −100° C. 4-Formylmorpholine (1.87 mL, 18.59 mmol) in diethyl ether (10 mL) was added all at once and the reaction was stirred for an additional 1 h. The mixture was then allowed to reach room temperature. Ammonium chloride saturated solution was added and the product was extracted with dichloromethane (3×70 mL). The combined organics were dried with magnesium sulfate, the solvent was evaporated and the residue was purified by flash chromatography eluting with 20% ethyl acetate in hexanes, to yield 0.44 g of 5-formyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 20a.

후처리

  1. additionAfter the addition
  2. stirringwas stirred for an additional 1 h
  3. customto reach room temperature
  4. extractionthe product was extracted with dichloromethane (3×70 mL)
  5. dry with materialThe combined organics were dried with magnesium sulfate
  6. customthe solvent was evaporated
  7. customthe residue was purified by flash chromatography
  8. washeluting with 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-5bc234eebe6d4b799fd9189d98124c56
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091200B2

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