Reaktion #2030409

Reaktionsgleichung

NaHCO3

(2R)-2-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione

8-fluoro-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

chloroform

sodium triacetoxyborohydride

→

title compound

Ausbeute 49.5%

(2R)-2-[(4-{[(8-Fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino}-1-piperidinyl)methyl]-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione hydrochloride

Ausbeute 49.5%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with 20% methanol/DCM (3×25 ml)
2. 2
   TrocknenThe combined organic extracts were dried (NaSO4)
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated
5. 5
   Sonstigepurified

Vorschrift

A suspension of (2R)-2-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione (for a preparation see Example 16A(j)) (58.5 mg, 0.194 mmol) and 8-fluoro-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde (for a synthesis see WO2007122258, Example 8(b)) (31.8 mg, 0.175 mmol) in chloroform (2 ml) and methanol (0.100 ml) at room temperature under nitrogen was stirred for 0.5 h. This was then treated with sodium triacetoxyborohydride (123 mg, 0.582 mmol) and stirred for 90 min. This was then treated with saturated aqueous NaHCO3 (10 ml) and extracted with 20% methanol/DCM (3×25 ml). The combined organic extracts were dried (NaSO4), filtered, evaporated and purified using silica chromatography (0-20% methanol/DCM) to give the free base of the title compound as a yellow gum (44.9 mg, 49.5%).

Quelle