Water → HCID 10245628, compound

HRID 622678Notes

Reaction equation

HRID 622678 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([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.C(N(CC)CC)C.C(Cl)(Cl)Cl.O.[CH2:31]=[C:32]1[O:36][C:34](=[O:35])[CH2:33]1>>[C:34]([O:18][CH:16]1[CH2:17][N:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:15]1)(=[O:35])[CH2:33][C:32]([CH3:31])=[O:36]

Participants

6

Reactant 5

HCID 962WaterHCID 6212ChloroformHCID 8471TriethylamineHCID 12661DiketeneHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 10245628HCID 10245628, compoundYield 93%

Procedure

11.95 g (0.05 mole) of 1-benzhydryl-3-hydroxyazetidine and 0.5 ml of triethylamine were dissolved in 50 ml of chloroform 6.3 g (0.075 mole) of diketene were then added dropwise to the solution, after which the reaction mixture was stirred for 10 hours at room temperature, and then water was added to it. The reaction mixture was then stirred for 30 minutes. At the end of this time, the chloroform layer was separated and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The concentrate was subjected to silica gel column chromatography, and 15.07 g (93%) of 1-benzhydryl-3-azetidinyl acetoacetate were obtained, as a pale yellow oil, from the fractions eluted with a 9:1 by volume mixture of toluene and ethyl acetate.

Workup

  1. additionwere then added dropwise to the solution
  2. stirringThe reaction mixture was then stirred for 30 minutes
  3. customAt the end of this time, the chloroform layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-53fd3db9b00142c7ace494de8f337569
Source dataset
uspto-grants-1988_09
Patent number
US04772596

Reaction notes

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