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

HRID 397057

반응식

HRID 397057 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cfd4df6734144854b362c5cba9d1839a
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608203B2

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