Reaction #302845

ord-2a07d52fd09c42aaa9ee8021c1fd9e17

Reaction equation

O=C(O)CCCC[C@@H](S)CCS
dihydrolipoic acid
C[N+](C)(C)C.[OH-]
tetramethylammonium hydroxide
CC(C)(C)[O-].[K+]
potassium t-butoxide
→
O=C(O)CCCC[C@@H]1CCSS1
lipoic acid
O=C(O)CCCC[C@@H](S)CCS
dihydrolipoic acid

Reactants

O=C(O)CCCC[C@@H](S)CCS
dihydrolipoic acid
C[N+](C)(C)C.[OH-]
tetramethylammonium hydroxide
CC(C)(C)[O-].[K+]
potassium t-butoxide

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08192646B2uspto-grants-2012_06