Cyclohexylamine → (R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid

HRID 1350273Notes

Reaction equation

HRID 1350273 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7]/[C:8](=[CH:12]\[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C1(N)CCCCC1>CO>[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]([OH:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 9835650(E)-2-[2-(tert-Butoxy)-2-oxoethyl]-5-phenyl-2-pentenoic acid

Product 1

HCID 10803584(R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acidYield 80.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of (E)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenyl-2-pentenoic acid (100 g, 0.34 mol), cyclohexylamine (39 ml, 0.34 mol) and [(S)-2,2′-bis(diphenylphosphino-1,1′-binaphthyl]chloro(p-cymene)ruthenium chloride (0.64 g, 0.69 mmol) in methanol (1000 ml) was heated to 60° C., under hydrogen (60 p.s.i.), for 42 hours and then allowed to cool to room temperature. The mixture was filtered through celite and then concentrated in vacuo to a yellow solid which was purified by re-crystallisation from acetone (850 ml). The resulting solid was partitioned between ethyl acetate (1200 ml) and citric acid solution (10%, 1200 ml) and the organic phase was separated, washed with demineralised water (1200 ml) and concentrated in vacuo to leave the title compound as an oil (80 g).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated in vacuo to a yellow solid which
  3. customwas purified by re-crystallisation from acetone (850 ml)
  4. customThe resulting solid was partitioned between ethyl acetate (1200 ml) and citric acid solution (10%, 1200 ml)
  5. customthe organic phase was separated
  6. washwashed with demineralised water (1200 ml)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d99a1f7ba5347f2ad67b47250d0bcc0
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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