Aluminium lithium hydride → (R)-Tert-butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1159089노트

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HRID 1159089 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10]([C@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:11]>CCOCC>[CH:10]([C@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:11]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 86597541(3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

생성물 1

HCID 57350014(R)-Tert-butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate수율 100%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

Lithium aluminum hydride (1 M in THF, 5.3 ml, 5.3 mmol) was added to a solution of (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.7 g, 5.0 mmol theory) in ether (16 ml) stirring at 0° C. under nitrogen. After stirring at 0° C. for 1 h, the reaction was slowly quenched with water (0.40 ml). Sodium hydroxide (1N, 0.80 ml) followed by water (0.60 ml) were then added and the resultant gelatinous precipitate was filtered through Celite® rinsing with ether and THF. The filtrate was evaporated and the residue transferred to a separatory funnel with EtOAc. Washing with brine and drying with MgSO4 afforded crude product (1.3 g, 100% yield) which was used in the next step without further purification.

후처리

  1. stirringAfter stirring at 0° C. for 1 h
  2. customthe reaction was slowly quenched with water (0.40 ml)
  3. additionwere then added
  4. filtrationthe resultant gelatinous precipitate was filtered through Celite®
  5. washrinsing with ether and THF
  6. customThe filtrate was evaporated
  7. customthe residue transferred to a separatory funnel with EtOAc
  8. washWashing with brine
  9. dry with materialdrying with MgSO4

출처 및 근거

ORD 기록
ord-9cde38c6b72548c5b9423c2011e50b47
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812024B2

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