Reaktion #2035669

Reaktionsgleichung

methylmagnesium bromide

(S)-ethyl 1-(2-(4-cyanophenyl)-2-oxoethyl)piperidine-3-carboxylate, hydrobromide

Sodium bicarbonate

hydroxylamine hydrochloride

→

(3S)-ethyl 1-(2-hydroxy-2-(4-((Z)-N′-hydroxycarbamimidoyl)phenyl)propyl)piperidine-3-carboxylate

Ausbeute 78.6%

Lösungsmittel

ethyl acetate

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with water
2. 2
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
3. 3
   Waschenwashed with saturated NaCl
4. 4
   TrocknenThe organic layer was dried with MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   workup.DISSOLUTIONThe crude residue was dissolved in 2-propanol (10 mL)
8. 8
   Waschenwashed with saturated NaCl
9. 9
   TrocknenThe organic layer was dried with MgSO4
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated

Vorschrift

To a mixture of (S)-ethyl 1-(2-(4-cyanophenyl)-2-oxoethyl)piperidine-3-carboxylate, hydrobromide (100 mg, 0.262 mmol) in THF (2 mL) was added methylmagnesium bromide (0.350 mL, 1.049 mmol). After 1 hour, the reaction was quenched with water. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried with MgSO4, filtered, and concentrated. The crude residue was dissolved in 2-propanol (10 mL). Sodium bicarbonate (88 mg, 1.049 mmol) and hydroxylamine hydrochloride (36.5 mg, 0.525 mmol) were added and the reaction was heated at 85° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried with MgSO4, filtered, and concentrated to yield 72 mg of (3S)-ethyl 1-(2-hydroxy-2-(4-((Z)-N′-hydroxycarbamimidoyl)phenyl)propyl)piperidine-3-carboxylate. MS (m+1)=350. HPLC Peak RT=0.11 minutes (Analytical Method B).

Quelle