Sodium hydride → HCID 58438115, compound

HRID 2092399Notes

Reaction equation

HRID 2092399 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].Br[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1)[CH3:19]>CN(C=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][N:11]([CH:18]([C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=2)[CH3:19])[C:10](=[O:14])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 1294739368120-55-8

Product 1

HCID 58438115HCID 58438115, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Boc-3-oxopiperazine (67 mg, 0.328 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 13 mg, 0.328 mmol). After cooling to 0° C., 1-(1-Bromo-ethyl)-4-iodo-benzene (100 mg, 0.273 mmol) was added. The ice bath was removed and the mixture stirred at RT for 2 h and then partitioned between EtOAc and a solution of NH4Cl. After separation, the aqueous phase was re-extracted twice with DCM and the combined organic extracts were washed with H2O, saturated brine, dried over Na2SO4, filtered and evaporated to dryness. The resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/EtOac] 1:0→0:1)) to yield the title intermediate (90 mg, 0.188 mmol, 68%) as a colorless solid. HPLC: FtRet=1.276.

Workup

  1. customThe ice bath was removed
  2. custompartitioned between EtOAc
  3. customAfter separation
  4. extractionthe aqueous phase was re-extracted twice with DCM
  5. washthe combined organic extracts were washed with H2O, saturated brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2
  10. washgradient elution, DCM/EtOac] 1:0→0:1))

Sources & evidence

ORD record
ord-55fa2f3a3f33474a860b0b6edc8aa141
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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