3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-Butyl 3-[(2-methylpropane-2-sulfinyl)imino]azetidine-1-carboxylate

HRID 509556

Reaction equation

HRID 509556 reaction equation
O=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[CH3:13][C:14]([S:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[C:14]([S:17]([N:19]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1)=[O:18])([CH3:16])([CH3:15])[CH3:13]

Participants

5

Reactant 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 56776988tert-Butyl 3-[(2-methylpropane-2-sulfinyl)imino]azetidine-1-carboxylateYield 24%

Reagents, catalysts & solvents 2

HCID 178477244HCID 178477244, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of tert-butyl 3-oxoazetidine-1-carboxylate (4 g, 23.37 mmol), 2-methylpropane-2-sulfinamide (3.12 g, 25.7 mmol) and tetraethoxytitanium (10.66 g, 46.7 mmol) in THF (40 ml) in a 20 ml sealed tube was stirred at 70° C. overnight. The reaction mixture was cooled to room temperature, quenched with water and filtered through a bed of Celite. The solid material was washed with ethyl acetate. The organic layer was separated, dried over Na2SO4, filtered and concentrated to obtain a crude mixture. The crude product was then purified by column chromatography (20% EtOAc in Hexane) to afford tert-butyl 3-(tert-butylsulfinylimino)azetidine-1-carboxylate Yield: 1.5 g (24%). 1H NMR (400 MHz, CDCl3): δ 5.15-4.94 (m, 1H), 4.75 (m, 1H), 4.68 (s, 2H), 1.45 (s, 9H), 1.27 (s, 9H).

Workup

  1. customsealed tube
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with water
  4. filtrationfiltered through a bed of Celite
  5. washThe solid material was washed with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto obtain a crude mixture
  11. customThe crude product was then purified by column chromatography (20% EtOAc in Hexane)

Sources & evidence

ORD record
ord-6457cae56dca409d9ce5a0a4b87ae24c
Source dataset
uspto-grants-2015_08
Patent number
US09096580B2

Linked notes

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