Acetic Acid → N-[(1R)-1-(1,3,4-oxadiazol-2-yl)propyl]cyclopentanamine

HRID 476129Notes

Reaction equation

HRID 476129 reaction equation
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C@H:6]([NH2:9])[CH2:7][CH3:8].[C:10]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C@H:6]([NH:9][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:7][CH3:8]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 28269085(1R)-1-(1,3,4-oxadiazol-2-yl)propan-1-amine

Product 1

HCID 68089400N-[(1R)-1-(1,3,4-oxadiazol-2-yl)propyl]cyclopentanamineYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1R)-1-(1,3,4-oxadiazol-2-yl)propan-1-amine (610 mg, 4.798 mmol) in THF (6.972 mL) was treated with cyclopentanone (407.6 mg, 428.6 μL, 4.846 mmol) then acetic acid (288.1 mg, 272.8 μL, 4.798 mmol). The reaction was stirred at ambient temperature for 20 minutes then treated with sodium triacetoxyborohydride (1.485 g, 7.005 mmol). The reaction was stirred at ambient temperature for 5 hours then basified with aqueous NaHCO3. The mixture was extracted with DCM (×10), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (50% EtOAc/petrol) to give the sub-title compound as a colourless solid (694 mg, 74%); 1H NMR (400.0 MHz, CDCl3) d 0.81 (3H, t), 1.10-1.87 (10H, m), 2.85 (1H, m), 3.95 (1H, t), 8.33 (1H, s); MS ES (+) 196.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 5 hours
  2. extractionThe mixture was extracted with DCM (×10)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (50% EtOAc/petrol)

Sources & evidence

ORD record
ord-098e9138272141fd9bd5f93f34df22fd
Source dataset
uspto-grants-2014_01
Patent number
US08637666B2

Reaction notes

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