Tert-butyl 3-hydroxyazetidine-1-carboxylate → 3-Oxo-azetidine-1-carboxylic acid tert-butyl ester

HRID 926702Notes

Reaction equation

HRID 926702 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([OH:23])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[O:23]=[C:21]1[CH2:22][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:20]1

Participants

4

Reactant 2

HCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PCC (4.94 g, 22.8 mmol) was added portion wise to a stirred solution of tert-butyl-3-hydroxyazetidine-1-carboxylate (3.3 g, 19 mmol) in DCM (50 mL) at 20-35° C. and the reaction mixture was stirred continuously at the same temperature for 12-16 h. The reaction mixture was filtered and the filtrate was washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude product, which was purified by column chromatography (using 60-120 silica gel and 10% EtOAc in Hexane as eluent) to afford 650 mg of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product, which
  6. customwas purified by column chromatography (using 60-120 silica gel and 10% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-74fa7afbe99449d3a6f7d8e0a51b866f
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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