Magnesium Chloride → HCID 12859196, compound

HRID 1381029Notes

Reaction equation

HRID 1381029 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]1C=CC=C[CH:21]=1.[Cl-].[Mg+2].[Cl-].C([Mg]Br)C>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])[CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 5360315Magnesium ChlorideHCID 6950385(S)-(+)-2-(Anilinomethyl)pyrrolidineHCID 12859191HCID 12859191, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 12859196HCID 12859196, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

2-Carbomethoxy-3-phenyl-1,3-diazabicyclo[3,3,0]octane prepared from 1.76 g of (S)-2-(anilinomethyl)pyrrolidine, as described in Example 8, was dissolved in 50 ml of THF, then admixed wtih 1.05 g of anhydrous magnesium chloride and refluxed by heating for 10 minutes. To the mixture cooled to -70° C., was added dropwise an ether solution containing 1.46 equivalents of ethylmagnesium bromide. The resulting mixture was treated as described in Example 12 to obtain 694 mg (28%) of 2-propionyl-3-phenyl-1,3-diazabicyclo[3,3,0]octane. NMR peaks: δ(ppm)=1.0 (3H, triplet), 1.4-2.1 (4H, multiplet), 2.1-2.6 (2H, multiplet), 2.6-3.3 (3H, multiplet), 3.5-3.9 (2H, multiplet), 4.2 (1H, singlet), 6.1-7.1 (5H, multiplet).

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 10 minutes
  3. additionThe resulting mixture was treated

Sources & evidence

ORD record
ord-bc9d2c72f233476fa7912cd969b5cdb7
Source dataset
uspto-grants-1986_04
Patent number
US04584387

Reaction notes

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