Sodium hydride → HCID 69057161, compound

HRID 2100634Notes

Reaction equation

HRID 2100634 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[NH:8][C@H:7]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C@@H:6]3[C:5]=2[CH:4]=1)[CH3:2].[H-].[Na+].[CH2:27](I)[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[N:8]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:7]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:17][C@@H:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28503Benzene, (2-iodoethyl)-HCID 69056703HCID 69056703, compound

Product 1

HCID 69057161HCID 69057161, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3aR,9bS)-tert-butyl 8-ethyl-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the first eluting peak from Example 74, Part B, (30 mg, 0.09 mmol) in 1 mL of DMF at ambient temperature was added sodium hydride (4 mg of 60% in mineral oil, 0.10 mmol) and phenethyliodide (33 mg, 0.14 mmol). The resulting mixture was allowed to stir at ambient temperature for 18 h. Starting material remained so the reaction was heated at 60° C. for 4 h. The reaction was quenched with water and extracted with ethyl acetate. The organics were washed with brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography (elution with 3:1 hexane ethyl acetate) to afford 16 mg (41%) of the title compound as an oil. LRMS (ESI): 435.4 (M+H)+.

Workup

  1. temperaturewas heated at 60° C. for 4 h
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (elution with 3:1 hexane ethyl acetate)

Sources & evidence

ORD record
ord-c7b6de1571b445e58ecdb212306800d6
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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