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

HRID 1712651Notes

Reaction equation

HRID 1712651 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH:10]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>O1CCCC1>[CH3:21][S:22]([O:8][CH2:9][CH:10]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]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

Triethylamine (1.80 ml) was added to a solution of tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (806 mg) in tetrahydrofuran (25 ml). This was cooled on ice under a nitrogen atmosphere, and methanesulfonyl chloride (0.499 ml) was added dropwise, followed by stirring at the same temperature for 30 minutes. The reaction mixture was partitioned after the 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 distilled off, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate). The fractions containing the target compound were concentrated to give the title compound (1.05 g, 92.0%) as a colorless oil.

Workup

  1. temperatureThis was cooled on ice under a nitrogen atmosphere
  2. customThe reaction mixture was partitioned
  3. additionafter the 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. distillationThe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate)
  9. additionThe fractions containing the target compound
  10. concentrationwere concentrated

Sources & evidence

ORD record
ord-d6f3c1d984dd413f8c8051ebf238b379
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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