Benzhydrylamine → trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-ol

HRID 1425382Notes

Reaction equation

HRID 1425382 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C@@H:16]([C@H:19]1[CH2:21][O:20]1)[CH2:17][CH3:18]>CO>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:14]2[CH2:21][C@@H:19]([OH:20])[C@@H:16]2[CH2:17][CH3:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 86648813HCID 86648813, compound

Product 1

HCID 86648812trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-olYield 48.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzhydrylamine (1.04 mL, 6.06 mmol) was added to a solution of (2R*)-2-[(1R*)-1-bromopropyl]oxirane obtained in Example (234a) (1.00 g, 6.06 mmol) in methanol (6 mL), and the mixture was heated under reflux for 17 hours. The reaction solution was concentrated under reduced pressure. Saturated aqueous sodium carbonate solution was added to the resulting residue, followed by extraction with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=2/1) to obtain 787 mg of the title compound as a colorless oily substance (49%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionSaturated aqueous sodium carbonate solution was added to the resulting residue
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  7. filtrationfiltration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-2b4925af887e46c0ad3b066a097ee00e
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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