1,4-Dioxane → 1-(4-(Cyclopropylmethoxy)phenyl)azetidin-3-ol

HRID 40576Notes

Reaction equation

HRID 40576 reaction equation
[Si]([O:8][CH:9]1[CH2:12][NH:11][CH2:10]1)(C(C)(C)C)(C)C.[CH:13]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=2)[CH2:15][CH2:14]1.CC([O-])(C)C.[Na+].O1CCOCC1>O>[CH:13]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([N:11]3[CH2:10][CH:9]([OH:8])[CH2:12]3)=[CH:20][CH:19]=2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 22676731HCID 22676731, compoundHCID 23676156Sodium t-butoxideHCID 574386563-((tert-Butyldimethylsilanyl)oxy)azetidine

Product 1

HCID 896223501-(4-(Cyclopropylmethoxy)phenyl)azetidin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

6.50 g (26.0 mmol) 3-(tert-butyldimethylsilyloxy)azetidine, 7.13 g (26.0 mmol) of 1-(cyclopropylmethoxy)-4-iodobenzene (WO2012/028676), 10.0 g (104 mmol) NaOtBu and 1.54 g (2.08 mmol) chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)(2-(2-aminoethyl)-phenyl)-palladium (II) are added to 65 mL dioxane and stirred at 75° C. for 2.5 h under inert gas atmosphere. Water is added and the resulting mixture is extracted with EtOAc. The org. layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo. The resulting crude product is purified by HPLC (ACN/H2O/NH3).

Workup

  1. extractionthe resulting mixture is extracted with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo
  5. customThe resulting crude product is purified by HPLC (ACN/H2O/NH3)

Sources & evidence

ORD record
ord-f4338d2c263e4f078d1440f51e9c44d9
Source dataset
uspto-grants-2013_09
Patent number
US08530460B2

Reaction notes

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