Water → (R)-tert-butyl 2-(tosyloxymethyl)azetidine-1-carboxylate

HRID 556686Notes

Reaction equation

HRID 556686 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:6][CH2:5][N:4]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.O>N1C=CC=CC=1>[S:20]([O:1][CH2:2][C@H:3]1[CH2:6][CH2:5][N:4]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 11074142(R)-1-Boc-2-azetidinemethanol

Product 1

HCID 11002347(R)-tert-butyl 2-(tosyloxymethyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Commercially available (R)-tert-butyl 2-(hydroxymethyl)azetidine-1-carboxylate (1.8 g, 9.61 mmol) in pyridine was treated with p-toluenesulfonyl chloride (1.83 g, 9.61 mmol). The reaction mixture was stirred at room temperature for 20 h then poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water (3×75 mL) and then dried (MgSO4), filtered, and concentrated in vacuo to afford the titled compound. MS (DCI) m/z 342 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water (3×75 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85587ce88bb64e0992bfe19ccfa12856
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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