Hydrogen chloride-ethyl acetate → 2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine

HRID 2383019ノート

反応式

HRID 2383019 の反応式
C(OC(=O)[NH:7][CH2:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:10])(C)(C)C.Cl.CCOC(C)=O>CCOC(C)=O>[CH:21]1([CH:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19][CH2:20][N:11]2[C:9](=[O:10])[CH2:8][NH2:7])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

参加物

4

反応物 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68250253Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate

生成物 1

HCID 593965892-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine収率 99.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate (1.5 g) was dissolved in EtOAc (20 mL), and 4 M HCl/EtOAc (3 mL) was added thereto under ice-cooling, followed by stirring at 50° C. for 5 hours. Then, the reaction solvent was evaporated. Saturated aqueous sodium bicarbonate was added to the reaction liquid which was then extracted with chloroform. The extract was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain 2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine (1.09 g).

後処理

  1. temperatureunder ice-cooling
  2. customThen, the reaction solvent was evaporated
  3. additionSaturated aqueous sodium bicarbonate was added to the reaction liquid which
  4. extractionwas then extracted with chloroform
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

出典と根拠

ORDレコード
ord-7a20500d789c4f14b5e2b2c6c8b218b9
出典データセット
uspto-grants-2012_09
特許番号
US08263607B2

反応ノート

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