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

HRID 1427043Notes

Reaction equation

HRID 1427043 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[C:13]([N:20]1[CH2:23][CH:22]([OH:24])[CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][S:2]([O:24][CH:22]1[CH2:23][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:21]1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (2.57 mL, 33.3 mmol) and triethylamine (11.6 mL, 83.1 mmol) were added to a solution of commercially available N—BOC-3-hydroxy azetidine (4.8 g, 27.7 mmol) in tetrahydrofuran (100 mL) under nitrogen atmosphere at room temperature. The reaction liquid was stirred at room temperature for 2 hours. A saturated aqueous sodium bicarbonate solution was added to the reaction liquid at room temperature, and the mixture was diluted with ethyl acetate. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1) to quantitatively obtain the title compound.

Workup

  1. customThe reaction liquid
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe drying agent was separated by filtration
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1)

Sources & evidence

ORD record
ord-9a3d6be0beb04131a599bd7f6e740e9b
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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