Triethylamine → tert-butyl 3-(N'-hydroxycarbamimidoyl)azetidine-1-carboxylate

HRID 2171981Notes

Reaction equation

HRID 2171981 reaction equation
[C:1]([CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)#[N:2].Cl.[NH2:15][OH:16].C(N(CC)CC)C>C(O)C>[NH2:2]/[C:1](=[N:15]\[OH:16])/[CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 106312831-Boc-3-cyanoazetidine

Product 1

HCID 88941927tert-butyl 3-(N'-hydroxycarbamimidoyl)azetidine-1-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 16 mL vial, tert-butyl 3-cyanoazetidine-1-carboxylate (190 mg, 1.04 mmol; which may be prepared as described in Step 2) was dissolved in ethanol (2.9 mL), then hydroxylamine hydrochloride (101 mg, 1.46 mmol) and triethylamine (247 μL, 1.77 mmol) were added. The reaction mixture was stirred at reflux for 3 h, cooled and concentrated. The residue was taken up in EtOAc and water, the aqueous layer extracted with EtOAc, dried over Na2SO4 and concentrated to give the product as a white solid (170 mg, 76%).

Workup

  1. temperatureat reflux for 3 h
  2. temperaturecooled
  3. concentrationconcentrated
  4. extractionwater, the aqueous layer extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-39f84efd62774eeda4ced1cdc9b14e05
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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