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

HRID 1159089ノート

反応式

HRID 1159089 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9cde38c6b72548c5b9423c2011e50b47
出典データセット
uspto-grants-2010_10
特許番号
US07812024B2

反応ノート

読み込み中…