Water → tert-Butyl 3-(methoxymethyl)azetidine-1-carboxylate

HRID 528751Notes

Reaction equation

[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:13][CH:12]([CH2:14][OH:15])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:16]I.O>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:13][CH:12]([CH2:14][O:15][CH3:16])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To 24.6 mg (0.74 mmol, 60% dispersion in mineral oil) NaH in 5 mL THF at 0° C. was added 0.115 g (0.61 mmol) 3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (prepared using route 15 step a) in 1 mL THF dropwise over 10 minutes, and the reaction was stirred at 0° C. for 30 minutes. 46 μL (0.74 mmol) methyl iodide was added and the reaction was stirred at room temperature for 2 hours. 20 mg (0.61 mmol, 60% dispersion in mineral oil) of NaH followed by 38 μL (0.61 mmol) of methyl iodide were added and the reaction mixture was stirred at room temperature for 16 hours. 5 mL of H2O was added and the mixture was extracted with EtOAc (2×10 mL), the organic layers were combined and dried with MgSO4. After filtration, the solvent was evaporated to give the desired product which was used for the next step without further purification.

Workup

customprepared
customdropwise over 10 minutes
stirringthe reaction was stirred at room temperature for 2 hours
additionwere added
stirringthe reaction mixture was stirred at room temperature for 16 hours
extractionthe mixture was extracted with EtOAc (2×10 mL)
dry with materialdried with MgSO4
filtrationAfter filtration
customthe solvent was evaporated

Sources & evidence

ORD record: ord-109e65e411d246dab2ed8ef7bb547e7b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346816B2

Reaction notes

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