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

HRID 1279810Notes

Reaction equation

HRID 1279810 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-5eb5eb684a7a4300b0df3e787163c8f8
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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