Oxalic Acid → (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate

HRID 517666

Reaktionsgleichung

Reaktionsgleichung von HRID 517666
[CH2:1]([O:8][NH:9][CH:10]1[CH2:15][NH:14][C@H:13]([C:16]#[N:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([OH:23])(=[O:22])[C:19]([OH:21])=[O:20]>C(OC(=O)C)C.CC(C)=O>[C:18]([OH:23])(=[O:22])[C:19]([OH:21])=[O:20].[CH2:1]([O:8][NH:9][CH:10]1[CH2:15][NH:14][C@H:13]([C:16]#[N:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 971Oxalic AcidHCID 117599345(2S)-5-[(benzyloxy)amino]-2-cyanopiperidine

Produkt 1

HCID 131732538(2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound of Formula (IX) was reacted with sulphuric acid and sodium triacetoxy borohydride, in presence of suitable solvent such as ethyl acetate and at temperature below −5° C., to provide (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine (X). The compound of Formula (X) was purified by forming oxalate salt. The compound of Formula (X) was reacted with oxalic acid in a mixture of ethylacetate and acetone to provide (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate (1:1) (XI), which was further treated with sodium hydrogen carbonate to obtain purified (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine (XII). The racemic compound (XI) was treated with methanol to obtain pure (2S,5R)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate.

Quellen und Nachweise

ORD-Eintrag
ord-74a80cbeac854130a1df403569ddc284
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115131B2

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