Tetramethylammonium hydroxide → Lipoic acid

HRID 215663

Reaction equation

HRID 215663 reaction equation
[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]

Participants

6

Reactant 3

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

Product 2

HCID 6112Lipoic acidHCID 9834298(R)-Dihydrolipoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Sources & evidence

ORD record
ord-2a07d52fd09c42aaa9ee8021c1fd9e17
Source dataset
uspto-grants-2012_06
Patent number
US08192646B2

Linked notes

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