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

HRID 2066274Notes

Reaction equation

HRID 2066274 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>O1CCCC1>[CH3:21][S:22]([O:1][CH2:2][CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)(=[O:24])=[O:23]

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 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (806 mg) in tetrahydrofuran (25 ml) was added triethylamine (1.80 ml). This was cooled in an ice bath under a nitrogen atmosphere, and methanesulfonyl chloride (0.499 ml) was added dropwise, followed by stirring at the same temperature for 30 min. The reaction mixture was partitioned after addition of ethyl acetate (100 ml) and water (70 ml). The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate). Fractions containing the target compound were concentrated to provide the titled compound as a colorless oil (1.05 g, 92.0%).

Workup

  1. temperatureThis was cooled in an ice bath under a nitrogen atmosphere
  2. customThe reaction mixture was partitioned
  3. additionafter addition of ethyl acetate (100 ml) and water (70 ml)
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate)
  9. additionFractions containing the target compound
  10. concentrationwere concentrated

Sources & evidence

ORD record
ord-a14b4bfbdb9c433b8d31a3fb595d1f7d
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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