Cyclohexylamine → HCID 69431039, compound

HRID 2084505Notes

Reaction equation

HRID 2084505 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([O:12][C:13](=[O:28])[CH2:14]/[C:15](=[CH:19]\[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)/[C:16]([OH:18])=[O:17])([CH3:11])([CH3:10])[CH3:9]>CO>[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([O:12][C:13](=[O:28])[CH2:14][C@@H:15]([CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]([OH:18])=[O:17])([CH3:11])([CH3:9])[CH3:10]

Participants

4

Reactant 2

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

Product 1

HCID 69431039HCID 69431039, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of cyclohexylamine (266 ml, 2.32 mol), (E)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenyl-2-pentenoic acid (Preparation 165, 688 g, 2.37 mol) and [(S)-2,2′-bis(diphenylphosphino-1,1′-binaphthyl]chloro(p-cymene)ruthenium chloride (4.4 g, 4.7 mmol) in methanol (6.9 liters) was heated to 60° C., under hydrogen (60 p.s.i.), for 47 hours and then allowed to cool to room temperature (enantiomeric excess=88%). The mixture was filtered through celite and then the solvent was stripped and replaced with acetone by distillation at atmospheric pressure, at a constant volume of 4.2 liters. The resulting suspension was cooled to room temperature where it was stirred for 4 hours and then filtered. The residue was washed with acetone (2×1 liter) and then dried in vacuo at 45° C. for 16 hours to leave the title compound as a colourless solid (590 g, 64% yield, enantiomeric excess=98.9%, 97% pure by HPLC).

Workup

  1. filtrationThe mixture was filtered through celite
  2. distillationreplaced with acetone by distillation at atmospheric pressure, at a constant volume of 4.2 liters
  3. temperatureThe resulting suspension was cooled to room temperature where it
  4. filtrationfiltered
  5. washThe residue was washed with acetone (2×1 liter)
  6. customdried in vacuo at 45° C. for 16 hours

Sources & evidence

ORD record
ord-2fc1aff284944b62a8436f4b0ca98e9e
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

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