Methanesulfonyl chloride → Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

HRID 887558Notes

Reaction equation

HRID 887558 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([CH2:12][OH:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[C:1]([N:8]1[CH2:9][CH:10]([CH2:12][O:13][S:15]([CH3:14])(=[O:17])=[O:16])[CH2:11]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-Boc-azetidin-3-yl)-methanol (1.06 g, 5.7 mmol), TEA (1.18 mL, 8.52 mmol) in CH2Cl2 at 0° C. was added MeSO2Cl (0.53 mL, 6.82 mmol) via a syringe. The reaction was warmed to RT over 2 h and stirring was continued at RT for 2 h. The white solid formed was removed by filtration and the filtrate was washed with 25 mL of H2O. The organic phase was dried over Na2SO4, and concentrated in vacuo to afford yellow oil.

Workup

  1. customThe white solid formed
  2. customwas removed by filtration
  3. washthe filtrate was washed with 25 mL of H2O
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto afford yellow oil

Sources & evidence

ORD record
ord-41055cb0c7e646dd84fd21527a748380
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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