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

HRID 1054450Notes

Reaction equation

HRID 1054450 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. 1H NMR (400 MHz, DMSO-d6) δ 4.66 (4H, s), 1.4 (9H, s) ppm.

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-841d5d78c0eb4bbda3f1cb64f3cd5db1
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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