(3R)-tert-Butyl 3-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxamido)piperidine-1-carboxylate → N-((R)-Piperidin-3-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445270

Reaktionsgleichung

Reaktionsgleichung von HRID 445270
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2[C:19]([NH:21][C@@H:22]2[CH2:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]2)=[O:20])=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O>[NH:24]1[CH2:25][CH2:26][CH2:27][C@@H:22]([NH:21][C:19]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:35])[F:36])=[CH:8][CH:7]=2)=[O:20])[CH2:23]1

Komponenten

3

Edukt 1

HCID 59536392(3R)-tert-Butyl 3-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxamido)piperidine-1-carboxylate

Produkt 1

HCID 59536393N-((R)-Piperidin-3-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of (3R)-tert-butyl 3-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-isoquinoline-2-carboxamido)piperidine-1-carboxylate (44 mg, 87 μmol, example 20) in TFA (30% in DCM, 2 mL) was stirred at RT for 30 min. The solvents were removed and EtOAc (5 mL) and saturated NaHCO3 (3 mL) were added to the residue. The solution mixture was then stirred at RT for 10 min. The organic layer was collected and the aqueous layer was extracted with EtOAc (2×2 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried under vacuum to give the title compound as an off-white solid. MS (ESI, positive ion) m/z: 404 (M+H).

Aufarbeitung

  1. customThe solvents were removed
  2. additionEtOAc (5 mL) and saturated NaHCO3 (3 mL) were added to the residue
  3. customThe organic layer was collected
  4. extractionthe aqueous layer was extracted with EtOAc (2×2 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-96671b9701f2407193dd2a1ed1ac3754
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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