HCID 15521821, compound → trans-10-Methylamino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-3-one

HRID 2304550Notes

Reaction equation

HRID 2304550 reaction equation
[CH3:1][N:2]=[C:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][N:5]2[C:13](=[O:16])[CH2:14][CH2:15][CH:4]12>CCO.[Pd]>[CH3:1][NH:2][C@@H:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][N:5]2[C:13](=[O:16])[CH2:14][CH2:15][C@H:4]12

Participants

4

Reactant 1

HCID 15521821HCID 15521821, compound

Product 1

HCID 54096343trans-10-Methylamino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-3-oneYield 6.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 10methylimino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-3-one (159 mg) and Pd/C (10%, 110 mg) in EtOH (10 mL) was hydrogenated in a shaker apparatus at 50 psi overnight, and then filtered. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel eluting with CH2Cl2/MeOH/NH4OH (150/8/1) to give an oil (11 mg): 1H NMR (300 MHz) δ 7.25 (m, 4 H), 4.92 (d, J=18.0 Hz, 1 H), 4.31 (d, J=17.7 Hz, 1 H), 3.95 (m, 1 H), 3.43 (d, J=2.7 Hz, 1 H), 2.38 (s, NCH3); MS (FAB), m/e 217 (100, M+H), 154 (55), 136 (45).

Workup

  1. customwas hydrogenated in a shaker apparatus at 50 psi overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was chromatographed on silica gel eluting with CH2Cl2/MeOH/NH4OH (150/8/1)

Sources & evidence

ORD record
ord-acbf86a1550446d58e8437fa912fb68a
Source dataset
uspto-grants-2002_08
Patent number
US06436954B1

Reaction notes

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