Ammonium formate → (S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate

HRID 1520763Notizen

Reaktionsgleichung

C1(C(=[N:14][C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]3[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]3)=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)=[CH:17][CH:16]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A suspension of (S)-tert-butyl 2-(4-(diphenylmethyleneamino)phenyl)morpholine-4-carboxylate (54.1 g, 122 mmol), ammonium formate (116 g, 1.83 mol) and Pd/C 5% (6.5 g, 3.06 mmol) in methanol (930 ml) was stirred at 60° C. for 2 h. The reaction mixture was filtered and concentrated. The residue was dissolved in ethyl acetate and water. The organic phase was extracted twice with 0.5M HCl. The combined aqueous phases were basified with 2M-NaOH and extracted twice with DCM. The organic phases were dried over magnesium sulfate, filtered and dried in vacuo, to yield 31.95 g off-white solid. MS (ISP): 279.1 ([M+H]+).

Aufarbeitung

filtrationThe reaction mixture was filtered
concentrationconcentrated
dissolutionThe residue was dissolved in ethyl acetate
extractionThe organic phase was extracted twice with 0.5M HCl
extractionextracted twice with DCM
dry with materialThe organic phases were dried over magnesium sulfate
filtrationfiltered
customdried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-1fbe18ed13bf4d389a72d5ab2a4a8bad
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09073911B2

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