Tetramethylammonium hydroxide → Lipoic acid

HRID 896940

Reaktionsgleichung

Reaktionsgleichung von HRID 896940
[OH-].C[N+](C)(C)C.CC(C)([O-])C.[K+].[CH2:13]([CH2:19][C@@H:20]([SH:24])[CH2:21][CH2:22][SH:23])[CH2:14][CH2:15][C:16]([OH:18])=[O:17]>CN(C=O)C>[CH2:21]1[C@@H:20]([CH2:19][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[S:24][S:23][CH2:22]1.[CH2:13]([CH2:19][C@@H:20]([SH:24])[CH2:21][CH2:22][SH:23])[CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Komponenten

6

Edukt 3

HCID 60966Tetramethylammonium hydroxideHCID 9834298(R)-Dihydrolipoic acidHCID 23665647Potassium tert-butoxide

Produkt 2

HCID 6112Lipoic acidHCID 9834298(R)-Dihydrolipoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In other synthetic schemes the base, tetramethylammonium hydroxide can be substituted for potassium t-butoxide in DMF. The former base though can be stored under air, whilst the latter needs to be kept in an inert atmosphere. The dihydrolipoic acid works best if it totally clear. If the reduction lipoic acid to produce dihydrolipoic acid is not complete, a yellow coloration of the solution will be evident. The yellow solution can be distilled (distills at 140° C. under vacuum) to yield a clear solution of dihydrolipoic acid.

Quellen und Nachweise

ORD-Eintrag
ord-dfa8a8fbcaf8412da0e392ebd82dc423
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921496B2

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