Acetonitrile → Tert-butyl 3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate

HRID 455002

Reaktionsgleichung

Reaktionsgleichung von HRID 455002
[C:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].BrN1C(C)(C)C(=O)N(Br)C1=[O:16].[C:24](#[N:26])C>>[OH:16][CH:11]1[CH:10]([NH:26][CH3:24])[CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:12]1

Komponenten

4

Edukt 3

HCID 6342AcetonitrileHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 5148195tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Produkt 1

HCID 21736783Tert-butyl 3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate

Versuchsvorschrift

N-Boc-3-pyrroline (1) (16 kg) was treated with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) (15.2 kg) in aqueous ACN to form the bromohydrin (2). After the reaction was complete, the excess brominating agent was quenched with aqueous sodium thiosulfate solution and the crude reaction mixture was treated with aqueous NaOH. The resulting epoxide was extracted with MTBE and the organic layer was concentrated to give the crude epoxide (3). This epoxide was added to 40% aqueous methylamine and, after the reaction was complete, the excess methylamine and water were removed by distillation and the product, (4), (18.5 kg) was isolated from diisopropyl ether.

Quellen und Nachweise

ORD-Eintrag
ord-549df69d72d144ea8860d72d6bdf7831
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497282B2

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