HCID 68292034, compound → HCID 68292597, compound

HRID 529446Notes

Reaction equation

HRID 529446 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][C@@H:6]([CH2:10][CH2:11][C@H:12]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:13]([OH:15])=[O:14])[C:7]([OH:9])=[O:8].[H][H]>CO.CCOC(C)=O.[Pd]>[CH2:5]([C@@H:6]([CH2:10][CH2:11][C@H:12]([CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[C:13]([OH:15])=[O:14])[C:7]([OH:9])=[O:8])[C:4]1[CH:23]=[CH:24][CH:25]=[CH:2][CH:3]=1

Participants

6

Reactant 2

HCID 68292034HCID 68292034, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68292597HCID 68292597, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,5R)-2-(3-chlorobenzyl)-5-(cyclohexylmethyl)hexanedioic acid (37 mg, 0.10 mmol) in MeOH (2 mL) and EtOAc (2 mL) was bubbled through Argon for 5 min. Then 5% Pd/C (40 mg) was added to the solution. The reaction was stirred at 1 atm of hydrogen (balloon) for 2 hr. The reaction was filtered through CELITE® and washed with MeOH. The combined filtrate and MeOH wash was concentrated. The resulting residue was purified using RP prep-HPLC (Method B). The desired fraction was concentrated in vacuum and lyophilized with CH3CN to give (2R,5R)-2-benzyl-5-(cyclohexylmethyl)hexanedioic acid (10 mg, 0.030 mmol, 30% yield) as a white solid.

Workup

  1. filtrationThe reaction was filtered through CELITE®
  2. washwashed with MeOH
  3. washThe combined filtrate and MeOH wash
  4. concentrationwas concentrated
  5. customThe resulting residue was purified
  6. concentrationThe desired fraction was concentrated in vacuum

Sources & evidence

ORD record
ord-a8f1b246d3d540bca8405c1731df48a6
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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