Triethylamine → Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

HRID 516145Notes

Reaction equation

HRID 516145 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(OCC)(=O)C>C(Cl)(Cl)Cl.O>[CH3:20][S:21]([O:12][CH:10]1[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)(=[O:23])=[O:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

N-Boc-3-hydroxyazetidine (1.73 g) was dissolved in chloroform (20 ml). Triethylamine (2.09 ml) and methanesulfonyl chloride (856 μl) were added thereto at 0° C. After stirring at room temperature for 0.5 hours, ethyl acetate and water were added thereto to separate the organic layer. After being washed with a saturated aqueous sodium bicarbonate solution, a saturated aqueous ammonium chloride solution, and water, the organic layer was dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain the title compound as a colorless, oily compound (2.32 g). Physical properties: m/z [M+H]+ 252.0

Workup

  1. customat 0° C
  2. customto separate the organic layer
  3. washAfter being washed with a saturated aqueous sodium bicarbonate solution
  4. dry with materiala saturated aqueous ammonium chloride solution, and water, the organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-e666a340e54c48fd8b72f935cf5971c0
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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