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

HRID 479611Notes

Reaction equation

HRID 479611 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 (100 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-d5e85a230ffe448183d36500c0a01b30
Source dataset
uspto-grants-2003_11
Patent number
US06645993B2

Reaction notes

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