Lithium hydroxide, monohydrate → 1-[(Tert-butoxy)carbonyl]azetidine-2-carboxylic acid

HRID 2177851Notes

Reaction equation

HRID 2177851 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][CH2:7][N:6]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:4].O.[OH-].[Li+]>O.O1CCOCC1>[C:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][CH:5]1[C:3]([OH:4])=[O:2])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 14821735Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 36238861-[(Tert-butoxy)carbonyl]azetidine-2-carboxylic acidYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Azetidine-1,2-dicarboxylic acid 1-t-butyl ester 2-methyl ester (1.0 g) was added to a solution of lithium hydroxide monohydrate (0.586 g) in water (6 ml) and dioxane (12 ml) and the resultant mixture was stirred at room temperature for 2.5 hours. The mixture was evaporated to dryness and ice cold 1M HCl was added to the cooled residue. DCM was added and the organic layer was separated and washed with water, brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give azetidine-1,2-dicarboxylic acid-1-t-butyl ester (0.925 g) as a colourless oil.

Workup

  1. customThe mixture was evaporated to dryness and ice cold 1M HCl
  2. additionwas added to the cooled residue
  3. additionDCM was added
  4. customthe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-617a5b9e120843d4950bff4cfa9b0fb2
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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