Ammonium Chloride → tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylate

HRID 1506151Notes

Reaction equation

HRID 1506151 reaction equation
C[Mg]Br.O1CCC[CH2:5]1.[O:9]=[C:10]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]1.[Cl-].[NH4+]>O1CCCC1>[OH:9][C:10]1([CH3:5])[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178420675HCID 178420675, compound

Product 1

HCID 54751705tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide-tetrahydrofuran solution (1.12 M, 3.90 mL, 4.38 mmol) was added dropwise to tert-butyl 3-oxoazetidine-1-carboxylate (500 mg, 2.92 mmol) in tetrahydrofuran (5 mL) under cooling with ice and stirred for 90 minutes. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1→1/1 (v/v)) to give the title compound as a colorless solid (224 mg, yield 41%).

Workup

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1→1/1 (v/v))

Sources & evidence

ORD record
ord-b72f481e991642e78d62e4bf4e65b4fb
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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