2-Propanol, 1-amino-2-methyl- → HCID 118468243, compound

HRID 629405Notes

Reaction equation

HRID 629405 reaction equation
[N:1]1([C:6]2[CH:26]=[CH:25][C:9]([CH2:10][C:11]3[C:12]([CH3:24])=[C:13]([CH3:23])[C:14]([CH:21]=O)=[C:15]([CH:20]=3)[C:16](OC)=[O:17])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[NH2:27][CH2:28][C:29]([CH3:32])([OH:31])[CH3:30]>C1COCC1>[OH:31][C:29]([CH3:32])([CH3:30])[CH2:28][N:27]1[CH2:21][C:14]2[C:15](=[CH:20][C:11]([CH2:10][C:9]3[CH:25]=[CH:26][C:6]([N:1]4[CH:5]=[CH:4][CH:3]=[N:2]4)=[CH:7][CH:8]=3)=[C:12]([CH3:24])[C:13]=2[CH3:23])[C:16]1=[O:17]

Participants

4

Reactant 2

HCID 951022-Propanol, 1-amino-2-methyl-HCID 118468262HCID 118468262, compound

Product 1

HCID 118468243HCID 118468243, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(4-(1H-pyrazol-1-yl)benzyl)-2-formyl-3,4-dimethylbenzoate (0.11 g) in THF (4.00 mL) was added 1-amino-2-methylpropan-2-ol (0.03 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, and the residue was diluted with methanol (4.0 mL). Sodium triacetoxyborohydride (0.11 g) was added thereto under argon atmosphere, and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.04 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with methanol (4.0 mL)
  3. additionSodium triacetoxyborohydride (0.11 g) was added
  4. stirringunder argon atmosphere, and the mixture was stirred overnight at room temperature
  5. additionTo the reaction mixture was added water
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-314ef879645948af9ee8956450d6b804
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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