HCID 11716184, compound → HCID 69056616, compound

HRID 2100602Notes

Reaction equation

HRID 2100602 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:11](=[O:13])[NH:10][C@H:9]3[CH2:14][NH:15][CH2:16][C@@H:8]3[C:7]=2[CH:6]=[C:5]([CH2:17][CH3:18])[CH:4]=1>CO.[Pd]>[ClH:2].[CH2:17]([C:5]1[CH:4]=[CH:3][C:12]2[C:11](=[O:13])[NH:10][C@H:9]3[CH2:14][NH:15][CH2:16][C@@H:8]3[C:7]=2[CH:6]=1)[CH3:18]

Participants

4

Reactant 1

HCID 11716184HCID 11716184, compound

Product 1

HCID 69056616HCID 69056616, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3aR,9bS)-6-chloro-8-ethyl-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one hydrochloride (the title compound of Example 29) (36 mg, 0.12 mmol) in 5 mL of methanol was added 10% Pd/C catalyst (2.5 mg). The mixture was stirred at room temperature under 1 atm of hydrogen maintained by a balloon for 3 h. The reaction mixture was filtered through a pad of Celite and concentrated in vacuo. The resulting solid was triturated with ether and dried in vacuo to afford 25 mg (80%) of the title compound of Example 40 as an off-white solid. 1H NMR (CD3OD): δ 7.91 (d, 1H, J=8.3 Hz), 7.32 (d, 1H, J=7.7 Hz), 7.10 (s, 1H), 4.10-4.03 (m, 1H), 3.80-3.68 (m, 2H), 3.47-3.39 (m, 2H), 3.30-3.25 (m, 1H), 2.72 (q, 2H, J=7.5 Hz), 1.25 (t, 3H, J=7.7 Hz). LRMS (ESI): 217.2 (M+H)+.

Sources & evidence

ORD record
ord-aefbd928938f471388766a570317eb47
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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