Reaktion #2358522

Reaktionsgleichung

Sodium triacetoxyborohydride

1-(3-fluoro-5-methylsulfonyl-phenoxy)propan-2-one

propylamine

acetic acid

→

1-(3-fluoro-5-methylsulfonyl-phenoxy)-N-propyl-propan-2-amine

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe suspension was filtrated
2. 2
   workup.ADDITIONsodium carbonate (100 ml, 10% aqueous solution) was added
3. 3
   ExtraktionThe aqueous phase was extracted with dichloromethane (3×50 ml)
4. 4
   TrocknenThe combined organic phase was dried with Na2SO4
5. 5
   Sonstigeevaporated
6. 6
   SonstigePurification on flash chromatography (ethyl acetate:methanol 1:0 to 4:1)

Vorschrift

Sodium triacetoxyborohydride (1.16 g, 5.51 mmol) was added to a stirred mixture of 1-(3-fluoro-5-methylsulfonyl-phenoxy)propan-2-one (0.905 g, 3.67 mmol), propylamine (0.24 g, 4.04 mmol), acetic acid (0.5 g, 8.33 mmol) and molecular sieves (2 g, 4 Å, 4-8 mesh) in dry 1,2-dichloroethane (20 ml) the mixture was stirred at ambient temperature for 24 h, the suspension was filtrated and sodium carbonate (100 ml, 10% aqueous solution) was added. The aqueous phase was extracted with dichloromethane (3×50 ml). The combined organic phase was dried with Na2SO4 and evaporated. Purification on flash chromatography (ethyl acetate:methanol 1:0 to 4:1). 0.3 g, 28%. MS m/z (relative intensity, 70 eV) 289 (M+, 1), 260 (9), 152 (4), 87 (6), 86 (bp).

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