Tetrahydrofuran → tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidine-1-carboxylate

HRID 43651

Reaktionsgleichung

Reaktionsgleichung von HRID 43651
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[O:15][CH2:16][CH3:17].C(=O)(O)[O-].[Na+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].C1COCC1>O>[CH2:27]([O:26][C:24]([NH:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][C@H:3]1[O:15][CH2:16][CH3:17])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 86648467Tert-butyl cis(+/-)-4-amino-3-ethoxypiperidine-1-carboxylate

Produkt 1

HCID 86648506tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidine-1-carboxylateAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The same operation as in Example (103a) was performed using tert-butyl cis(±)-4-amino-3-ethoxypiperidine-1-carboxylate obtained in Example (112d) (2.28 g, 11.4 mmol), sodium bicarbonate (1.26 g, 15 mmol), benzyl chloroformate (2.69 g, 15 mmol), THF (15 mL) and water (15 mL). The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1) to obtain 4.34 g of the title compound as a colorless solid (100%).

Aufarbeitung

  1. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-ba6eeb1eb1494158a4c26172d78026ef
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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