Benzyl 3-(3-methyl-5-oxo-4,5,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-1-yl)-pyrrolidine-1-carboxylate → 3-Methyl-1-pyrrolidin-3-yl-3,4,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-5-one

HRID 1034960Notes

Reaction equation

HRID 1034960 reaction equation
[CH3:1][N:2]1[C:6]2[NH:7][C:8](=[O:15])[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[C:5]=2[C:4]([CH:16]2[CH2:20][CH2:19][N:18](C(OCC3C=CC=CC=3)=O)[CH2:17]2)=[N:3]1>ClCCl.CO.[Pd]>[CH3:1][N:2]1[C:6]2[NH:7][C:8](=[O:15])[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[C:5]=2[C:4]([CH:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)=[N:3]1

Participants

5

Reactant 1

HCID 136353285Benzyl 3-(3-methyl-5-oxo-4,5,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-1-yl)-pyrrolidine-1-carboxylate

Product 1

HCID 1359489453-Methyl-1-pyrrolidin-3-yl-3,4,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-5-oneYield 110.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 24E (766 mg, 1.88 mmol) in a mixture of dichloromethane (30 mL) and methanol (30 mL) was treated with 10% palladium on carbon (150 mg) under hydrogen at ambient temperature for 6 hours. Solid material was filtered off and the filtrate concentrated to provide the title compound (564 mg, 100%). 1H NMR (DMSO-d6): 1.67-1.79 (m, 4H), 2.01-2.11 (m, 1H), 2.22-2.32 (m, 1H), 2.38-2.43 (m, 2H), 2.85-2.91 (m, 2H), 3.16-3.26 (m, 2H), 3.30 (dd, J=11.0, 8.0 Hz, 1H), 3.46 (dd, J=11.2, 7.5 Hz, 1H), 3.78 (s, 3H), 3.81-3.88 (m, 1H).

Workup

  1. filtrationSolid material was filtered off
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-a22c684307fe4da59dfc73bff01f13b3
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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