Reaktion #689284

Reaktionsgleichung

cis-tert-butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

6-(3-fluorophenyl)nicotinic acid

HATU

DIPEA

→

cis-tert-butyl-3-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)-4-hydroxypyrrolidine-1-carboxylate

Ausbeute 58.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed in vacuo
2. 2
   workup.ADDITIONthe residue diluted with ethyl acetate and water
3. 3
   SonstigeThe layers were separated
4. 4
   Waschenthe organic layer washed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigethe solvent removed
7. 7
   Sonstigeto give an oil, which after chromatography (silica, 65% ethyl acetate:hex)

Vorschrift

To a solution of 6-(3-fluorophenyl)nicotinic acid (391 mg, 1.8 mmol ) in DMF (10 mL) at 0° C. was added HATU (753 mg, 1.98 mmol) and DIPEA (0.47 mL, 2.07 mmol ). After 15 min, cis-tert-butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate was added and the reaction stirred at room temperature for 5 hrs. The solvent was removed in vacuo and the residue diluted with ethyl acetate and water. The layers were separated and the organic layer washed with brine, dried (MgSO4) and the solvent removed to give an oil, which after chromatography (silica, 65% ethyl acetate:hex) to give the desired product, cis-tert-butyl-3-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)-4-hydroxypyrrolidine-1-carboxylate (420 mg, 58%). LC/MS (M+H)=401.9 observed, 402.18 expected.

Quelle