Magnesium Chloride → HCID 12859198, compound

HRID 851243Notes

Reaction equation

HRID 851243 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]=CC=C[CH:21]=1.[Cl-].[Mg+2].[Cl-].C([Mg]Br)(C)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])[CH:20]([CH3:25])[CH3:21]

Participants

7

Reactant 4

HCID 5360315Magnesium ChlorideHCID 6950385(S)-(+)-2-(Anilinomethyl)pyrrolidineHCID 12859191HCID 12859191, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 12859198HCID 12859198, compoundYield 79%

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 637 mg of (S)-2-(anilinomethyl)pyrrolidine was dissolved in 18 ml of THF, then admixed with 378 mg of anhydrous magnesium chloride, and refluxed for 10 minutes by heating. To the mixture cooled to -70° C., was added dropwise an ether solution containing 1.37 equivalents of isopropylmagnesium bromide. The resulting mixture was treated as in Example 12 to obtain 731 mg (79%) of 2-isobutyryl-3-phenyl-1,3-diazabicyclo[3,3,0]octane. NMR peaks: δ (ppm)=0.9 (3H, doublet), 1.1 (3H, doublet), 1.5-2.2 (4H, multiplet), 2.4-3.3 (4H, multiplet), 3.5-3.9 (2H, multiplet), 4.4 (1H, singlet), 6.2-7.1 (5H, multiplet).

Workup

  1. temperaturerefluxed for 10 minutes
  2. temperatureby heating
  3. additionThe resulting mixture was treated as in Example 12

Sources & evidence

ORD record
ord-2eb69143e5a640f68da7d96e4560367a
Source dataset
uspto-grants-1983_05
Patent number
US04383122

Reaction notes

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