Borane;tetrahydrofuran → 4-(5-Oxazolyl)benzylamine

HRID 2042015Notes

Reaction equation

HRID 2042015 reaction equation
[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=O)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.B.C1COCC1>C1COCC1>[O:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][NH2:12])=[CH:13][CH:14]=2)=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 219309994-(5-Oxazolyl)-benzamide

Product 1

HCID 219309934-(5-Oxazolyl)benzylamineYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 4-(5-oxazolyl)benzamide (500 mg, 2.657 mmol) in 10 mL of dry THF was cooled to 0° C. and 10 mL of 1 M BH3.THF (10.00 mmol) was added. The contents were refluxed overnight and the excess borane was destroyed by dropwise addition of methanol. The solvent was evaporated and the residue was treated with methanolic HCl to decompose the amine-borane complex. After evaporation of the methanol, the residue was taken in water, basified to pH 10 and the product was extracted in to DCM. The DCM layer was dried (K2CO3) and the solvent was removed to provide 150 mg (32%) of 4-(5-oxazolyl)benzylamine: 1H NMR (CDCl3) δ 7.90 (s, 1H), 7.60 (d, 2H), 7.40 (d, 2H), 7.30 (s, 1H), 3.90 (s, 2H).

Workup

  1. temperatureThe contents were refluxed overnight
  2. customthe excess borane was destroyed by dropwise addition of methanol
  3. customThe solvent was evaporated
  4. additionthe residue was treated with methanolic HCl
  5. customAfter evaporation of the methanol
  6. extractionthe product was extracted in to DCM
  7. dry with materialThe DCM layer was dried (K2CO3)
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-0600f35303fb4dd3bf44dda8544e8ac6
Source dataset
uspto-grants-2013_11
Patent number
US08586576B2

Reaction notes

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