Reaktion #2316447

Reaktionsgleichung

title compound

1′-[2-[[(1,1-Dimethylethyloxycarbonyl)-2-amino-2-methyl-1-oxopropyl)amino]-1-oxo-3-(phenylmethoxy)propyl]spiro-[1H-indene-1,4′-piperidine]-3-carboxylic Acid Methyl Ester

methylene chloride ethyl acetate

Tellurium

sodiumborohydride

→

title compound

Ausbeute 90.9%

1′-[2-[[(1,1-Dimethylethyloxycarbonyl)-2-amino-2-methyl- 1-oxopropyl)amino]-1-oxo-3-(phenylmethoxy)propyl]-2,3-dihydrospiro[1H-indene-1,4′-piperidine]-3-carboxylic Acid Methyl Ester

Ausbeute 90.9%

Lösungsmittel

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 10 minutes
2. 2
   Sonstigewas cannulated into the reaction mixture at room temperature
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
6. 6
   workup.ADDITION1 N KOH was added
7. 7
   ExtraktionThe aqueous layer was then extracted with ethyl acetate (3×1 vol)
8. 8
   TrocknenThe organic layers were dried over anhydrous sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated

Vorschrift

To a suspention of Tellurium (52.6 mg, 0.412 mmol) in ethanol (2.0 ml) was added sodiumborohydride (36.6 mg, 0.99 mmol) and the mixture was refluxed for 10 minutes. A solution of the title compound from Example 3, Step E (100 mg, 0.165 mg) in ethanol (1.0 ml) was cannulated into the reaction mixture at room temperature. The reaction mixture was then stirred over night, filtered and concentrated. The residue was dissolved in ethyl acetate and 1 N KOH was added. The aqueous layer was then extracted with ethyl acetate (3×1 vol). The organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. Flash chromatography (silica gel, methylene chloride/ethyl acetate 2:1) gave the title compound (91 mg, 0.15 mmol) as a clear glass.

Quelle