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

HRID 633881Notes

Reaction equation

HRID 633881 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-88fc899244994e0c85b4d1ebf520c892
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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