(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 445270Notes

Reaction equation

HRID 445270 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-96671b9701f2407193dd2a1ed1ac3754
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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