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

HRID 2383314
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HRID 2383314 반응식
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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-69a402ed1e9840edb9fe71de1cf2eb9b
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263620B2

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