Diethyl Ether → tert-butyl-2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetate

HRID 68223Notes

Reaction equation

HRID 68223 reaction equation
[C:1]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl-].[C:14]([O:18][C:19](=[O:22])[CH2:20][Zn+])([CH3:17])([CH3:16])[CH3:15].CCOCC>C1COCC1>[C:14]([O:18][C:19](=[O:22])[CH2:20][C:10]1([OH:12])[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178451183HCID 178451183, compound

Product 1

HCID 58520848tert-butyl-2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of N-Boc-3-azetidinone (0.45 g, 2.64 mmol) in THF (5 mL) was slowly added a 0.5 M solution of 2-tert-butoxy-2-oxoethyl-zinc chloride in Et2O (10 mL, 5.0 mmol), and the reaction mixture was stirred for 5 h. The reaction was then quenched with sat. aq. NH4Cl (10 mL), and the aqueous layer was separated and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with 5% aq. NaHCO3 (2×10 mL), brine (15 mL), dried over Na2SO4, filtered and concentrated to dryness to yield tert-butyl-2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetate (MS m/e [M+H]+ calcd 288.2. found 287.7).

Workup

  1. customThe reaction was then quenched with sat. aq. NH4Cl (10 mL)
  2. customthe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. washThe combined organic layers were washed with 5% aq. NaHCO3 (2×10 mL), brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-05547141b5f2496c85acf69650ed38b3
Source dataset
uspto-grants-2014_09
Patent number
US08822424B2

Reaction notes

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