Lithium Hydroxide → 2-(1-(Tert-butoxycarbonyl)azetidin-3-yl)acetic acid

HRID 1177417Notes

Reaction equation

HRID 1177417 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][C:13]([O:15]CC)=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1.CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([CH2:12][C:13]([OH:15])=[O:14])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15256325Tert-butyl 3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate

Product 1

HCID 110959892-(1-(Tert-butoxycarbonyl)azetidin-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-ethoxycarbonylmethyl-azetidine-1-carboxylic acid tert-butyl ester (2.3 g, 0.095 mol) in 30 mL THF/MeOH/water (3:2:1) was added (0.477 g, 11.35 mmol) of LiOH*H2O at 0° C. The reaction mixture was stirred for 3 h at 25° C. Methanol and THF were removed in vacuo, and the reaction mixture was diluted with 50 mL water, and extracted with ethyl acetate. The aqueous layer was acidified with 2N HCl, extracted with ethyl acetate, and the organic layer was dried over Na2SO4, and concentrated to give 2-(1-(tert-butoxycarbonyl)-azetidin-3-yl)acetic acid. 1H-NMR (400 MHz, CDCl3), δ ppm 4.12-4.07 (m, 2H), 3.66-3.60 (m, 2H), 2.91-2.84 (m, 1H), 2.68-2.66 (m, 2H), 1.43 (s, 9H).

Workup

  1. customMethanol and THF were removed in vacuo
  2. additionthe reaction mixture was diluted with 50 mL water
  3. extractionextracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-71dd6ab163af4206a5941bd7a8e35049
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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