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Lithium borohydride → 1,1-Dimethylethyl 6-cyano-1-(2-hydroxyethyl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 2383314
ノート
印刷プレビュー

反応式

HRID 2383314 の反応式
C([O:5][C:6](=O)[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:20])[C:14]([C:18]#[N:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])CCC.[BH4-].[Li+]>C(O)C.C(OCC)C>[C:18]([C:14]1[C:13]([CH3:20])=[C:12]2[C:17](=[CH:16][CH:15]=1)[CH:8]([CH2:7][CH2:6][OH:5])[N:9]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:10][CH2:11]2)#[N:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 4148881Lithium borohydrideHCID 595910861,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

生成物 1

HCID 595910851,1-Dimethylethyl 6-cyano-1-(2-hydroxyethyl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate収率 96.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether
溶媒

実験手順

To a solution of 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 18; 2.15 g, 5.56 mmol) in ethanol (10 ml) and diethyl ether (40 ml) was added lithium borohydride (2M solution in tetrahydrofuran, 4.17 ml; 8.34 mmol) at 25° C. under nitrogen. After 1.5 h at 25° C., the solvent was removed, and the residue dissolved in ethyl acetate. The solution was washed with 1N hydrochloric acid, and the aqueous layer further extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, dried over MgSO4 and concentrated in vacuo to give the title compound (1.70 g) as a white foam.

後処理

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe solution was washed with 1N hydrochloric acid
  4. extractionthe aqueous layer further extracted with ethyl acetate
  5. washThe combined organic phases were washed with saturated sodium bicarbonate
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-69a402ed1e9840edb9fe71de1cf2eb9b
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263620B2

反応ノート

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