HCID 68292420, compound → HCID 68292680, compound

HRID 529445Notes

Reaction equation

HRID 529445 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][C@@H:6](/[CH:10]=[CH:11]/[C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])[C:7]([OH:9])=[O:8].[H][H]>C1COCC1.[Pt](=O)=O>[CH:4]1([CH2:5][C@@H:6]([CH2:10][CH2:11][C@H:12]([CH2:16][CH:17]2[CH2:18][CH2:19][CH:20]([O:23][CH3:24])[CH2:21][CH2:22]2)[C:13]([OH:15])=[O:14])[C:7]([OH:9])=[O:8])[CH2:25][CH2:26][CH2:27][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 68292420HCID 68292420, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68292680HCID 68292680, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,5S,E)-2-(3-chlorobenzyl)-5-(4-methoxybenzyl)hex-3-enedioic acid (113 mg, 0.291 mmol) in THF (5 mL) was added platinum(IV) oxide (60 mg, 0.26 mmol). The reaction was stirred at 1 atm of hydrogen (balloon) for 16 h. The reaction was filtered through CELITE® and washed with MeOH. The combined filtrate and MeOH washing was concentrated to give (2R,5R)-2-(cyclohexylmethyl)-5-((4-methoxycyclohexyl)methyl)hexanedioic acid (105 mg, 0.287 mmol, 98.5 yield) as an oil. Anal. Calcd. for C20H27ClO4 m/z 366.4. found: 365.3 (M−H)+.

Workup

  1. filtrationThe reaction was filtered through CELITE®
  2. washwashed with MeOH
  3. concentrationThe combined filtrate and MeOH washing was concentrated

Sources & evidence

ORD record
ord-f1bad6ef837b4dd2a130b0a0a49fc992
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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