Ethyl Acetate → HCID 86670539, compound

HRID 333883Notes

Reaction equation

HRID 333883 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.CCN([CH:11]([CH3:13])[CH3:12])C(C)C.CN([C:17]([O:21]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:38][CH2:39]OC(C)=O>C(Cl)Cl>[N:1]1([C:17](=[O:21])[C:11]([CH3:12])([CH3:13])[C:38]#[CH:39])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86670539HCID 86670539, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,1-dimethyl-3-butynoic acid (333 mg, 3.0 mmol), azetidine (250 mg, 4.5 mmol) and i-Pr2NEt (1.6 mL, 8.9 mmol) in CH2Cl2 (20 mL) was added solid HATU (1.25 g, 3.3 mmol). The mixture was stirred at rt for 20 h and concentrated to leave a yellow oil. This oil was taken up in EtOAc (100 mL), washed with 5% aq HCl (2×15 mL), satd aq NaHCO3 (15 mL) and brine (15 mL), and dried over Na2SO4. Removal of the solvent left an oil (819 mg) which was purified by chromatography on a 12-g silica cartridge, eluted with a 0-100% EtOAc in hexanes gradient, to afford 1-(azetidin-1-yl)-2,2-dimethylbut-3-yn-1-one (198 mg, 44%) as an oil. 1H NMR (CDCl3) 1.40 (s, 6H), 2.23 (m, 2H), 2.34 (s, 1H), 4.05 (m, 2H), 4.52 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customto leave a yellow oil
  3. washwashed with 5% aq HCl (2×15 mL)
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent
  6. waitleft an oil (819 mg) which
  7. customwas purified by chromatography on a 12-g silica cartridge
  8. washeluted with a 0-100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-5005f355fd2244bbb0528e2facba937d
Source dataset
uspto-grants-2014_11
Patent number
US08883778B2

Reaction notes

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