Methanol → HCID 68687822, compound

HRID 1296300Notes

Reaction equation

HRID 1296300 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:10]=1[CH2:11][N:12]([CH2:18][C@H:19]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][NH:20]1)[C:13](=[O:17])[CH:14](Cl)[CH3:15].CCOC(C)=O.CO>CN(C=O)C.C(Cl)Cl>[CH3:7][O:8][C:9]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:10]=1[CH2:11][N:12]1[C:13](=[O:17])[CH:14]([CH3:15])[N:20]2[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[CH2:28][C@@H:19]2[CH2:18]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 68688549HCID 68688549, compound

Product 1

HCID 68687822HCID 68687822, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Cesium carbonate (0.18 g) was added to a solution of N-(2,4-dimethoxybenzyl)-2-chloro-N-(((3R)-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl)propanamide (0.18 g, 0.44 mmol) in DMF (4.7 ml). After stirring at ambient temperature for 3 h, the reaction was transferred to a separatory funnel with EtOAc. Extraction with EtOAc, washing the organic layer with water (3×) and brine and drying over MgSO4 afforded 0.15 g of crude product. Flash chromatography (SiO2, 0.2 to 10% MeOH in CH2Cl2) gave pure product (0.11 g, 68%). MS (ESI) 367 (M+H).

Workup

  1. extractionExtraction with EtOAc
  2. washwashing the organic layer with water (3×) and brine
  3. dry with materialdrying over MgSO4
  4. customafforded 0.15 g of crude product

Sources & evidence

ORD record
ord-daf19ee59b7745b0a4c75cbf6a5e2366
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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