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

HRID 2099363ノート

反応式

HRID 2099363 の反応式
CON(C)[C:4]([C@H:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][N:7]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH:4]([C@H:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][N:7]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:5]

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 58%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

7.4 g of tert-butyl (3R)-3-{[methoxy(methyl)-amino]carbonyl}-3,4-dihydroisoquinoline-2(1H)-carboxylate are dissolved in 31 ml of diethyl ether under N2. The reaction medium is placed at 0° C. and 0.98 g of lithium aluminium hydride is carefully added. The mixture is stirred at 0° C. for 45 min. After hydrolysis with an aqueous potassium sulphate solution, extraction is carried out with diethyl ether until the aqueous phase is completely depleted. The organic phases are washed with a 3N aqueous hydrochloric acid solution, with a saturated aqueous sodium hydrogen carbonate solution, then with H2O, and finally with a saturated aqueous sodium chloride solution. Drying over MgSO4 and concentration to dryness are carried out. 3.5 g of tert-butyl (3R)-3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate are obtained, which product is subsequently used as it is.

後処理

  1. customis placed at 0° C.
  2. customAfter hydrolysis
  3. extractionwith an aqueous potassium sulphate solution, extraction
  4. washThe organic phases are washed with a 3N aqueous hydrochloric acid solution, with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialDrying over MgSO4 and concentration to dryness

出典と根拠

ORDレコード
ord-2ad90f2d7ef24cfead33b144fd9d7f83
出典データセット
uspto-grants-2009_08
特許番号
US07569582B2

反応ノート

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