Diethyl Ether → Benzyl 3-hydroxy-3-methylazetidine-1-carboxylate

HRID 1922701Notes

Reaction equation

HRID 1922701 reaction equation
C[Mg]Br.[CH3:4]COCC.[CH2:9]([O:16][C:17]([N:19]1[CH2:22][C:21](=[O:23])[CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH2:9]([O:16][C:17]([N:19]1[CH2:22][C:21]([OH:23])([CH3:4])[CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10632047Benzyl 3-oxoazetidine-1-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 59606083Benzyl 3-hydroxy-3-methylazetidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 3.0 M solution of methylmagnesium bromide in Et2O (0.98 mL, 2.92 mmol), at 0° C., was added a solution of 3-oxoazetidine-1-carboxylic acid benzyl ester (0.5 g, 2.44 mmol) in anhydrous THF (5 mL) dropwise over 5 min under argon. The reaction mixture was stirred for 18 h at room temperature, and then quenched by addition of a saturated aqueous solution of NH4Cl (2.5 mL) and water (5 mL). The aqueous phase was extracted with EtOAc (10 mL) The organic layer was separated, dried over sodium sulphate and concentrated in vacuo to give 3-Hydroxy-3-methylazetidine-1-carboxylic acid benzyl ester as a colourless oil (0.54 g, 99%). LCMS (Method A): RT=3.60 min, [M+H]+ 221.9

Workup

  1. customquenched by addition of a saturated aqueous solution of NH4Cl (2.5 mL) and water (5 mL)
  2. extractionThe aqueous phase was extracted with EtOAc (10 mL) The organic layer
  3. customwas separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d24970f6becb4467ae69188c457ca526
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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