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

HRID 1161845Notes

Reaction equation

HRID 1161845 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxymethylazetidine-1-carboxylic acid tert-butyl ester (for preparation see: Askew, B., et al., US 20033225106) (0.3 g, 1.60 mmol) in DCM (3 mL) was added Et3N (1 mL, 7.17 mmol), followed by methanesulfonyl chloride (0.5 mL, 6.46 mmol) and the reaction mixture stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo, the residue dissolved in DCM and the organic phase washed with saturated sodium bicarbonate (aq.). The organic layer was dried (MgSO4), and concentrated in vacuo to give 3-methanesulfonyloxymethylazetidine-1-carboxylic acid tert-butyl ester (0.36 g, 1.40 mmol, 85%) as an oil which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in DCM
  3. washthe organic phase washed with saturated sodium bicarbonate (aq.)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acd72740269a4b0396d78c4fd014cef9
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

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