Reaktion #1462275

Reaktionsgleichung

sodium borohydride

sodium borohydride

[1-(4-{(benzotriazol-1-ylmethyl)-amino}-phenyl)-cyclopentyl]-acetic acid tert-butyl ester

sodium borohydride

→

title compound

Ausbeute 100.3%

[1-(4-Methylamino-phenyl)-cyclopentyl]-acetic acid tert-butyl ester

Ausbeute 100.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITwas continued for a further hour
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas continued for a further hour
5. 5
   SonstigeThe reaction mixture was then evaporated
6. 6
   workup.ADDITIONthe residue was treated with water (15 mL) and ethyl acetate (25 mL)
7. 7
   SonstigeThe organic phase was separated
8. 8
   Waschenwashed with water (15 mL)
9. 9
   Trocknenwith brine (15 mL), then dried over magnesium sulfate
10. 10
    Sonstigeevaporated

Vorschrift

A stirred suspension of [1-(4-{(benzotriazol-1-ylmethyl)-amino}-phenyl)-cyclopentyl]-acetic acid tert-butyl ester (0.21 g) in ethanol (10 mL), under argon, was treated with sodium borohydride (0.051 g). After stirring at room temperature for 2 hours a further aliquot of sodium borohydride (0.017 g) was added and stirring was continued for a further hour, then a further aliquot of sodium borohydride (0.017 g) was added and stirring was continued for a further hour. The reaction mixture was then evaporated and the residue was treated with water (15 mL) and ethyl acetate (25 mL). The organic phase was separated and then washed with water (15 mL), then with brine (15 mL), then dried over magnesium sulfate and then evaporated to give the title compound (0.15 g) as an amber oil which crystallised on standing.

Quelle