Tetrahydrofuran → HCID 67187209, compound

HRID 717593Notes

Reaction equation

HRID 717593 reaction equation
[N:1]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][C@H:2]1C(OC)=O.C([Mg]Br)C.[CH2:29]1[CH2:33][O:32]C[CH2:30]1>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[OH:32][C:33]1([C@@H:2]2[CH2:3][N:4]([C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])[CH2:5][CH2:6][N:1]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 573569521,4-Di-tert-butyl 2-methyl (2S)-piperazine-1,2,4-tricarboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 67187209HCID 67187209, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

To a solution of (S)-1,4-di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate (3 g; 8.7 mmol) and titanium tetraisopropoxide (0.77 ml; 2.6 mmol), cooled to 0° C. under N2, a 3M solution of ethyl magnesium bromide in THF (8.7 ml; 26 mmol) was added dropwise over 45 minutes. The reaction mixture was left to warm up to room temperature and stirred for 18 hours. The reaction mixture was quenched with a 1M hydrochloric acid aqueous solution. The reaction mixture was diluted with water. Extractions were carried out with ethyl acetate. The combined organics were backwashed with a saturated sodium bicarbonate aqueous solution and brine. The organic was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silica gel (40 g), eluting with petrol/ethyl acetate (0 to 40%). The product was obtained as colourless oil (1.4 g; 50%). 1H NMR (CDCl3) 1.37-1.41 (18H, m), 1.52 (4H, s), 2.80-2.90 (1H, m), 3.10-3.40 (2H, m), 3.50-3.70 (2H, m), 3.80-4.20 (2H, m).

Workup

  1. waitThe reaction mixture was left
  2. customThe reaction mixture was quenched with a 1M hydrochloric acid aqueous solution
  3. additionThe reaction mixture was diluted with water
  4. extractionExtractions
  5. dry with materialThe organic was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified on silica gel (40 g)
  9. washeluting with petrol/ethyl acetate (0 to 40%)
  10. customThe product was obtained as colourless oil (1.4 g; 50%)

Sources & evidence

ORD record
ord-135db661598f46ce8ae548e80c2d82f8
Source dataset
uspto-grants-2015_11
Patent number
US09193722B2

Reaction notes

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