Water → tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylate

HRID 1021313Notes

Reaction equation

HRID 1021313 reaction equation
[O:1]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[CH2:13]1COCC1.C[Mg]Br.C1COCC1.O>CCOC(C)=O>[OH:1][C:2]1([CH3:13])[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178420675HCID 178420675, compound

Product 1

HCID 54751705tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-oxoazetidine-1-carboxylate (1 g) and THF (20 ml), which had been cooled to 0° C., were mixed, and a 1.12 M methylmagnesium bromide/THF solution (10 ml) was added thereto, followed by stirring at the same temperature for 1 hour. Water and EtOAc were added to the reaction mixture, the organic layer was dried over Na2SO4, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain tert-butyl 3-hydroxy-3-methylazetidine-1-carboxylate (1.0 g).

Workup

  1. additionwere mixed
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-44b4bcd9b57f4d15b80b61d4ae4b3d64
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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