HCID 20345304, compound → HCID 21406199, compound

HRID 972198Notes

Reaction equation

HRID 972198 reaction equation
[CH:1]([N:14]1[CH2:17][CH2:16][CH:15]1[C:18](=[N:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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[Li]>CCOCC>[CH:1]([N:14]1[CH2:17][CH2:16][CH:15]1[CH:18]([NH:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 20345304HCID 20345304, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 21406199HCID 21406199, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Cool to 0° C a solution of 1.0 g. of 1-benzhydryl-2-[α-(N-trifluoroacetylimino)benzyl]azetidine (from step A) in 25 ml of ether. To this solution, add 1.3 ml of a 2 molar ethereal solution of methyllithium. Maintain the reaction mixture at 0° C for 1 hour, then allow to stand at room temperature for two hours. Cool the mixture in an ice bath and quench by careful dropwise addition of 45 ml of saturated aqueous ammonium chloride solution. Dilute the mixture with additional ether and water, separate the layers, and wash the organic phase successively with water and saturated aqueous sodium chloride solution. Dry over anhydrous sodium sulfate and remove solvent in vacuo to obtain the title compound.

Workup

  1. temperatureMaintain the reaction mixture at 0° C for 1 hour
  2. temperatureCool the mixture in an ice bath
  3. customquench by careful dropwise addition of 45 ml of saturated aqueous ammonium chloride solution
  4. additionDilute the mixture with additional ether and water
  5. customseparate the layers
  6. washwash the organic phase successively with water and saturated aqueous sodium chloride solution
  7. dry with materialDry over anhydrous sodium sulfate
  8. customremove solvent in vacuo

Sources & evidence

ORD record
ord-fe084280dd4a49168d4e4b60b32c0279
Source dataset
uspto-grants-1977_10
Patent number
US04052383

Reaction notes

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