Ammonium Chloride → HCID 12859200, compound

HRID 1381031Notes

Reaction equation

HRID 1381031 reaction equation
[C:1]([CH:5]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH:10]2[N:6]1[CH2:7][CH2:8][CH2:9]2)([O:3]C)=O.N(C[C@@H]1CCCN1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[Mg+2].[Cl-].C1([Mg]Br)C=CC=CC=1.[Cl-].[NH4+]>C1COCC1.CCOCC>[C:1]([CH:5]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH:10]2[N:6]1[CH2:7][CH2:8][CH2:9]2)(=[O:3])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 5360315Magnesium ChlorideHCID 6950385(S)-(+)-2-(Anilinomethyl)pyrrolidineHCID 12859191HCID 12859191, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 12859200HCID 12859200, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

2-Carbomethoxy-3-phenyl-1,3-diazabicyclo[3,3,0]octane prepared from 181 mg of (S)-2-(anilinomethyl)pyrrolidine was dissolved in 5.5 ml of THF, then admixed with 108 mg of anhydrous magnesium chloride, and heated and refluxed for 10 minutes. To the mixture cooled to -70° C., was added dropwise 1.38 equivalents of phenylmagnesium bromide dissolved in ether. After having been stirred at -70° C. for 15 minutes, the reaction mixture was admixed with saturated aqueous ammonium chloride solution and ether, and brought to room temperature. The mixture was extracted with ether and the ether layer was washed with 1N aqueous sodium hydroxide solution and then with saturated aqueous sodium chloride solution. After drying, the ether layer was freed from the solvent by distillation under reduced pressure. The oily residue was purified by alumina column chromatography to obtain 230 mg (77%) of 2-benzoyl-3-phenyl-1,3-diazabicyclo[3,3,0]octane. NMR peaks: δ(ppm)=1.6-2.2 (4H, multiplet), 2.4-3.9 (5H, multiplet), 5.4 (1H, singlet), 6.1-7.9 (10H, multiplet).

Workup

  1. temperatureheated
  2. temperaturerefluxed for 10 minutes
  3. custombrought to room temperature
  4. extractionThe mixture was extracted with ether
  5. washthe ether layer was washed with 1N aqueous sodium hydroxide solution
  6. customAfter drying
  7. distillationthe ether layer was freed from the solvent by distillation under reduced pressure
  8. customThe oily residue was purified by alumina column chromatography

Sources & evidence

ORD record
ord-22e63977c83a4e9ab472a0a75065799d
Source dataset
uspto-grants-1986_04
Patent number
US04584387

Reaction notes

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