Reaction #543549

ord-fed8c9324be34a5a8e6c9e26c2754501

Reaction equation

[BH4-].[Na+]
NaBH4
CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=O)C(C)(C)CCC1
9-cis-retinaldehyde
CC1=C(/C=C/C(C)=C/C(C)C/C(C)=C\CO)C(C)(C)CCC1
13-cis-retinol
→
CC1=C(/C=C/C(C)=C\C=C\C(C)=C\CO)C(C)(C)CCC1
9-cis-Retinol

Reactants

[BH4-].[Na+]
NaBH4
CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=O)C(C)(C)CCC1
9-cis-retinaldehyde
CC1=C(/C=C/C(C)=C/C(C)C/C(C)=C\CO)C(C)(C)CCC1
13-cis-retinol

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Othersubsequently purified by normal phase HPLC essentially as we
  2. 2
    Otherhave described for 11-cis-retinol synthesis and purification (25)

Procedure

All-trans-retinol was obtained as a gift from Dr. Christian Eckhoff of Hoffmann-LaRoche, Inc. (Nutley, N.J.), and 13-cis-retinol was purchased from Sigma. 9-cis-Retinol was synthesized by NaBH4 reduction of authentic 9-cis-retinaldehyde (Sigma) and subsequently purified by normal phase HPLC essentially as we have described for 11-cis-retinol synthesis and purification (25). All-trans-, 13-cis-, and 9-cis-retinaldehydes were purchased from Sigma.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07186534B1uspto-grants-2007_03