4-Methylmorpholine → Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate

HRID 2383017ノート

反応式

HRID 2383017 の反応式
Cl.[CH:2]1([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][NH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(Cl)(=O)C(C)(C)C.CN1CCOCC1.[C:32]([O:36][C:37]([NH:39][CH2:40][C:41](O)=[O:42])=[O:38])([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl.O>[C:32]([O:36][C:37](=[O:38])[NH:39][CH2:40][C:41]([N:9]1[CH2:10][CH2:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]1[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:42])([CH3:35])([CH3:33])[CH3:34]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 62493Pivaloyl chlorideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 675358401-Cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

生成物 1

HCID 68250253Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate収率 100.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.00 g) was dissolved in methylene chloride (20 mL), and pivaloyl chloride (0.98 mL) and 4-methylmorpholine (2.2 mL) were added thereto under ice-cooling. The reaction liquid was stirred at room temperature for 30 minutes and then ice-cooled, and [(tert-butoxycarbonyl)amino]acetic acid (1.54 g) was added thereto. The reaction liquid was stirred at room temperature for 14 hours and then water was added thereto, followed by extraction with chloroform. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate (1.49 g).

後処理

  1. temperatureunder ice-cooling
  2. customThe reaction liquid
  3. temperatureice-cooled
  4. customThe reaction liquid
  5. stirringwas stirred at room temperature for 14 hours
  6. extractionfollowed by extraction with chloroform
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

出典と根拠

ORDレコード
ord-4e31b68b89a2401bbc988e2a880062c6
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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