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

HRID 397084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397084
[C:1]1([S:7]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20]CC4C=CC=CC=4)[CH:16]=3)[CH:11]2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:30][CH:29]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[C:1]1([S:7]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:20])[CH:16]=3)[CH:11]2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:30][CH:29]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 178141212-Benzenesulfonyl-6-benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 101842122-Benzenesulfonyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-olAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-benzenesulfonyl-6-benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline (0.043 g, 0.08 mmol), ammonium formate (0.096 g, 1.52 mmol), and 20% Pd(OH)2/C (0.025 g) in MeOH (10 ml) was refluxed under N2 for 1 hr, then filtered through Celite. The filtrate was evaporated in vacuo to a white residue that was dissolved in CH2Cl2 (10 ml) and washed with 1M NaOH (5 ml). The aqueous layer was extracted with CH2Cl2 (3×10 ml), and all of the combined organic solutions were dried over MgSO4 and concentrated in vacuo to give 0.026 g (72% yield) of colorless residue.

Aufarbeitung

  1. temperaturewas refluxed under N2 for 1 hr
  2. filtrationfiltered through Celite
  3. customThe filtrate was evaporated in vacuo to a white residue that
  4. dissolutionwas dissolved in CH2Cl2 (10 ml)
  5. washwashed with 1M NaOH (5 ml)
  6. extractionThe aqueous layer was extracted with CH2Cl2 (3×10 ml)
  7. dry with materialall of the combined organic solutions were dried over MgSO4
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4d928dd33d5c4b3cbdee4217da9662ec
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608203B2

Notizen zur Reaktion

Wird geladen…