3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylate

HRID 1054451Notes

Reaction equation

HRID 1054451 reaction equation
[CH3:1][Mg]Br.[O:4]=[C:5]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1>C1COCC1>[OH:4][C:5]1([CH3:1])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1

Participants

4

Reactant 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178418573HCID 178418573, compound

Product 1

HCID 54751705tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylateYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium bromide (3.0M in Diethyl ether) (1.5 mL, 4.5 mmol) was added to cold (−10° C.) solution of tert-butyl 3-oxoazetidine-1-carboxylate (650 mg, 3.8 mmol) in THF (10 mL) and stirring was continued at 20-35° C. for 1 h. After which the reaction mixture was quenched with saturated aqueous NH4Cl solution and extracted with ethylacetate. The organic layer separated was washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the residue. The residue was purified by column chromatography (using 60-120 silica gel and 50% EtOAc in Hexane as eluent) to afford 430 mg of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 5.56 (1H, s), 3.7-3.5 (4H, m), 1.4 (9H, s), 1.3 (3H, s) ppm.

Workup

  1. customAfter which the reaction mixture was quenched with saturated aqueous NH4Cl solution
  2. extractionextracted with ethylacetate
  3. customThe organic layer separated
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customto afford the residue
  8. customThe residue was purified by column chromatography (using 60-120 silica gel and 50% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-91aa2330090740829d8937a26aff6796
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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