(+-)-2-Butanol → 2-phenyl-1-(1-phenyl-1H-1,2,3-triazol-5-yl)ethanamine

HRID 1506626

Reaction equation

HRID 1506626 reaction equation
[C:1]1([N:7]2[C:11]([C:12]#[N:13])=[CH:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([Mg]Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(O)CC.[BH4-].[Na+]>O1CCCC1.CO>[C:15]1([CH2:14][CH:12]([C:11]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[N:9][CH:10]=2)[NH2:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 6568(+-)-2-ButanolHCID 4311764Sodium borohydrideHCID 846537091-phenyl-1H-1,2,3-triazole-5-carbonitrileHCID 178418336HCID 178418336, compound

Product 1

HCID 902812472-phenyl-1-(1-phenyl-1H-1,2,3-triazol-5-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9C (280 mg, 1.63 mmol) in tetrahydrofuran (5 mL), benzylmagnesium chloride (2M in THF) (1.23 mL, 2.46 mmol) was added dropwise. After 3 hours, 3 mL of 2-butanol was added to the reaction and sodium borohydride (0.5 g) was added to the mixture by portion. The reaction was monitored by LC/Mass until it was done. Methanol (5 mL) was added to the mixture. The organic layer was washed with brine and extracted with ethyl acetate (50 mL twice). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was purified by flash column (Rf: 0.3, 3% MeOH/DCM) to provide the desired product. MS (m/z) 265 [M+H]+.

Workup

  1. additionwas added to the mixture by portion
  2. washThe organic layer was washed with brine
  3. extractionextracted with ethyl acetate (50 mL twice)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column (Rf: 0.3, 3% MeOH/DCM)

Sources & evidence

ORD record
ord-55b96b07b7ae4eed898402a7696ec0dc
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Linked notes

Loading…