Sodium borohydride → 1-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445255ノート

反応式

HRID 445255 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 57326486HCID 57326486、化合物

生成物 1

HCID 166406961-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (4.69 g, 17 mmol) in MeOH (24 mL) was added sodium borohydride (1.94 g, 51.1 mmol) slowly at 0° C. Then, the mixture was stirred at 0° C. for 15 min and at RT for 2 h. The solvent was then removed and H2O (20 mL) was added to the residue. A saturated NaHCO3 solution (150 mL) was added slowly and the mixture was extracted with EtOAc (2×200 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was mixed with silica gel (4:1; residue:silica gel) and purified by silica gel chromatography (20%-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 278 (M+H).

後処理

  1. customThe solvent was then removed
  2. additionH2O (20 mL) was added to the residue
  3. additionA saturated NaHCO3 solution (150 mL) was added slowly
  4. extractionthe mixture was extracted with EtOAc (2×200 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated
  7. additionThe residue was mixed with silica gel (4:1; residue:silica gel)
  8. custompurified by silica gel chromatography (20%-100% EtOAc/hexane)

出典と根拠

ORDレコード
ord-e915530bbd774fc89c538eff496f0229
出典データセット
uspto-grants-2013_07
特許番号
US08476297B2

反応ノート

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