Water → HCID 68690353, compound

HRID 1159107Notes

Reaction equation

HRID 1159107 reaction equation
[CH2:1]([N:8]1[CH2:23][CH2:22][N:11]2[C:12](=[O:21])[C:13]3[CH:14]=[C:15](Br)[CH:16]=[CH:17][C:18]=3[CH2:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([Cu])#[N:25].CCOC(C)=O.O>CN1CCN(C)C1=O.[Cu]I>[CH2:1]([N:8]1[CH2:23][CH2:22][N:11]2[C:12](=[O:21])[C:13]3[CH:14]=[C:15]([C:24]#[N:25])[CH:16]=[CH:17][C:18]=3[CH2:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 58911635HCID 58911635, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 68690353HCID 68690353, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
190 °C

Procedure

Mixture of (R)-2-benzyl-8-bromo-1,2,3,4,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-6-one (25 mg, 0.067 mmol), CuCN (12.9 mg, 0.14 mmol) and CuI (3.7 mg, 0.29 mmol) in 1,3-dimethyl-2-imidazolidinone (1.5 mL) was stirred at 190° C. for 83 min in microwave. The reaction was cooled to RT and added EtOAc (20 mL) and H2O (5 mL). Filtered off the precipitate and rinsed with EtOAc (50 mL). The organic layer was separated and washed with brine (5 mL), dried over MgSO4, and conc in vacuo to give crude product. Purified by prep TLC (SiO2, 95:5, CH2Cl2:MeOH) to yield crude product as a yellow oil. MS (ESI) 318 (M+H).

Workup

  1. temperatureThe reaction was cooled to RT
  2. filtrationFiltered off the precipitate
  3. washrinsed with EtOAc (50 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (5 mL)
  6. dry with materialdried over MgSO4
  7. customconc in vacuo to give crude product
  8. customPurified by prep TLC (SiO2, 95:5, CH2Cl2:MeOH)
  9. customto yield crude product as a yellow oil

Sources & evidence

ORD record
ord-801a2a3ee19d4aa4839e7a3f4e65648e
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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