1-Benzhydryl-3-(2-tert-butylphenoxy)azetidine → 3-(2-Tert-butylphenoxy)azetidine

HRID 2041959Notes

Reaction equation

HRID 2041959 reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1>CO.[Pd]>[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][CH:16]1[CH2:15][NH:14][CH2:17]1)([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 1

HCID 595771511-Benzhydryl-3-(2-tert-butylphenoxy)azetidine

Product 1

HCID 534095303-(2-Tert-butylphenoxy)azetidineYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzhydryl-3-(2-tert-butylphenoxy)azetidine (9.10 g, 24.5 mmol) and 10% Pd/C (10% on carbon, 1.90 g) in methanol (300.0 mL) was stirred under hydrogen atmosphere (1 atm) at room temperature. After 24 h the reaction mixture was filtered through a pad of Celite, the Celite pad was washed with methanol and the filtrate was concentrated under reduced pressure. Purification by flash column chromatography (silica gel; 70:30 to 0:100 heptane/ethyl acetate, 98:2 ethyl acetate/methanol, 90:9:1 ethyl acetate/methanol/7.0 N ammonia-methanol) provided 3-(2-tert-butylphenoxy)azetidine (2.00 g, 40%) as a yellow oil.

Workup

  1. filtrationAfter 24 h the reaction mixture was filtered through a pad of Celite
  2. washthe Celite pad was washed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customPurification by flash column chromatography (silica gel; 70:30 to 0:100 heptane/ethyl acetate, 98:2 ethyl acetate/methanol, 90:9:1 ethyl acetate/methanol/7.0 N ammonia-methanol)

Sources & evidence

ORD record
ord-89073dd8b9344da5b69354ceed0d1733
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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