Reaktion #168305

Reaktionsgleichung

tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate

sodium borohydride

→

tert-butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 16 hours at room temperature
2. 2
   SonstigeThe mixture was quenched with saturated aqueous ammonium chloride
3. 3
   Einengenconcentrated
4. 4
   ExtraktionThe resulting residue was extracted with DCM (3×)
5. 5
   Trocknenthe combined extracts were dried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated

Vorschrift

To a solution of tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate (500 mg, 2.37 mmol) in methanol (4.7 mL) at 0° C. was added sodium borohydride (134 mg, 3.55 mmol). The reaction mixture was stirred at 0° C. for 1 hour and then stirred for 16 hours at room temperature. The mixture was quenched with saturated aqueous ammonium chloride and concentrated. The resulting residue was extracted with DCM (3×) and the combined extracts were dried over sodium sulfate, filtered, and concentrated to afford tert-butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate. 1H NMR (500 MHz, CDCl3) δ 4.35 (broad, 1H), 4.13 (s, 2H), 2.28-2.19 (m, 1H), 2.18-2.12 (m, 1H), 1.83-1.75 (m, 1H), 1.71-1.68 (m, 1H), 1.66-1.56 (m, 1H), 1.56-1.48 (m, 1H), 1.44 (s, 9H), 1.05 (dd, J=3.4, 12.7, 1H).

Quelle