Ammonium formate → 1-[4-(2-Pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-ol

HRID 397057

反応式

HRID 397057 の反応式
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)[NH:14][CH2:13][CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[N:28]1([CH2:27][CH2:26][O:25][C:22]2[CH:23]=[CH:24][C:19]([CH:15]3[C:16]4[C:11](=[CH:10][C:9]([OH:8])=[CH:18][CH:17]=4)[CH2:12][CH2:13][NH:14]3)=[CH:20][CH:21]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 181724176-Benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 181724491-[4-(2-Pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-ol収率 56.1%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

実験手順

A mixture of 6-benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline (0.300 g, 0.70 mmol), ammonium formate (0.883 g, 14.0 mmol), and 20% Pd(OH)2/C (0.050 g) in MeOH (50 ml) was refluxed under N2 for 1 hr, then filtered through Celite®. The filtrate was evaporated in vacuo to a yellow residue that was suspended in a mixture of H2O (5 ml) and saturated NaHCO3 solution (5 ml), then extracted with CH2Cl2 (4×10 ml). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to give 0.133 g of yellow oil. The aqueous layer was extracted again with CH2Cl2 (4×50 ml) to give an additional 0.083 g of yellow oil, for a total of 0.216 g (91% yield) of product.

後処理

  1. temperaturewas refluxed under N2 for 1 hr
  2. filtrationfiltered through Celite®
  3. customThe filtrate was evaporated in vacuo to a yellow residue that
  4. additionwas suspended in a mixture of H2O (5 ml) and saturated NaHCO3 solution (5 ml)
  5. extractionextracted with CH2Cl2 (4×10 ml)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cfd4df6734144854b362c5cba9d1839a
出典データセット
uspto-grants-2003_08
特許番号
US06608203B2

関連ノート

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