3-Hydroxyazetidine hydrochloride → (3,5-Di-tert-butyl-4-hydroxy-phenyl)-(3-hydroxy-azetidin-1-yl)-methanone

HRID 1766968Notes

Reaction equation

HRID 1766968 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.[C:7]([C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[C:14](Cl)=[O:15])([CH3:10])([CH3:9])[CH3:8]>[OH-].[Na+].C1COCC1>[C:21]([C:18]1[CH:17]=[C:13]([C:14]([N:2]2[CH2:5][CH:4]([OH:6])[CH2:3]2)=[O:15])[CH:12]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:19]=1[OH:20])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 11645178(3,5-Di-tert-butyl-4-hydroxy-phenyl)-(3-hydroxy-azetidin-1-yl)-methanoneYield 30%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
-5 °C

Procedure

Azetidin-3-ol hydrochloride (2 g, 18,3 mmoles) was dissolved in a 5% weight/weight (45 ml) of an aqueous solution of sodium hydroxide, the resulting solution cooled to −5° C. and under vigorous stirring 3,5-di-tert-butyl-4-hydroxy-benzoyl chloride (5,4 g, 20 mmoles) obtained according to step (a) dissolved in 8 ml of THF was added. Afterwards the cooling bath was removed, the reaction mixture warmed to room temperature (approximately 25° C.) and stirred for an additional hour under these conditions. The reaction mixture was then extracted several times with diethyl ether, the etherical phases combined, washed with water, dried with sodium sulfate and evaporated to dryness to obtain 1,9 g of the crude product, which is crystallized from ethyl acetate-petroleum ether. 1,6 g (30% of theoretical yield) of (3,5-di-tert-butyl-4-hydroxy-phenyl)-(3-hydroxy-azetidin-1-yl)-methanone were obtained in crystalline form.

Workup

  1. customobtained
  2. additionwas added
  3. customAfterwards the cooling bath was removed
  4. temperaturethe reaction mixture warmed to room temperature (approximately 25° C.)
  5. extractionThe reaction mixture was then extracted several times with diethyl ether
  6. washwashed with water
  7. dry with materialdried with sodium sulfate
  8. customevaporated to dryness
  9. customto obtain 1,9 g of the crude product, which
  10. customis crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-1279ba48fc04498ca542b43889c41df6
Source dataset
uspto-grants-2007_06
Patent number
US07232812B2

Reaction notes

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