Hydrochloric Acid → HCID 58817881, compound

HRID 457392Notes

Reaction equation

HRID 457392 reaction equation
[CH2:1]([N:5]1[C:9]([C@@H:10]([NH:15]N2CCC[C@@H]2COC)[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:8][N:7]=[C:6]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:2][CH2:3][CH3:4].B.C1COCC1.Cl>C1COCC1>[CH2:1]([N:5]1[C:9]([C@H:10]([NH2:15])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:8][N:7]=[C:6]1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 69513733HCID 69513733, compound

Product 1

HCID 58817881HCID 58817881, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 193 (1.43 g, 3.6 mmol) under argon in anhydrous THF (25 mL) at room temperature is slowly added borane-THF complex (1 M in THF, 54 ml, 54 mmol). The mixture is then refluxed under argon for 16 h. After cooling to room temperature, 10% HCl (20 mL) is added very slowly and the mixture is stirred for 2 h at room temperature. The organic solvent is removed under reduced pressure and the residue is extracted with ether. The aqueous phase is saturated with solid potassium carbonate and extracted with sthyl acetate. The residue obtained after removal of the solvent is purified by column chromatography to afford the desired product as a colorless oil. Yield: 0.6 g; LC-MS (MH+): 286.

Workup

  1. customat room temperature
  2. temperatureThe mixture is then refluxed under argon for 16 h
  3. customThe organic solvent is removed under reduced pressure
  4. extractionthe residue is extracted with ether
  5. extractionextracted with sthyl acetate
  6. customThe residue obtained
  7. customafter removal of the solvent
  8. customis purified by column chromatography

Sources & evidence

ORD record
ord-b5d7c4a02f2546ecbfb76f59fb444fc5
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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