(R)-(+)-3-Chlorostyrene oxide → (1R)-1-(3-chlorophenyl)-2-[3-(3-ethoxycarbonylmethoxyphenyl)cyclohexylamino]ethanol

HRID 1108776Notes

Reaction equation

HRID 1108776 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=2)[O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:3]1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C@H:25]1[O:27][CH2:26]1>C(O)C>[Cl:21][C:22]1[CH:23]=[C:24]([C@@H:25]([OH:27])[CH2:26][NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][CH:4]([C:8]3[CH:20]=[CH:19][CH:18]=[C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=3)[CH2:3]2)[CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 18784179HCID 18784179, compound

Product 1

HCID 9912456(1R)-1-(3-chlorophenyl)-2-[3-(3-ethoxycarbonylmethoxyphenyl)cyclohexylamino]ethanolYield 61.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-(3-aminocyclohexyl)phenoxyacetate (8.47 g) was dissolved in ethanol (50 ml), and (R)-3-chlorostyrene oxide (4.72 g) was added prior to heating to reflux for 7.5 hours. After allowing the mixture to cool, the solvent was concentrated under reduced pressure to obtain an oily substance which was then separated and purified by silica gel column chromatography (n-hexane:ethyl acetate=1:5), to give 8.15 g of (1R)-1-(3-chlorophenyl)-2-[3-(3-ethoxycarbonylmethoxyphenyl) cyclohexylamino]ethanol (trans-H) (compound of Example 11) as an oily substance (61.8% yield).

Workup

  1. temperatureto heating
  2. temperatureto reflux for 7.5 hours
  3. temperatureto cool
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customto obtain an oily substance which
  6. customwas then separated
  7. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=1:5)

Sources & evidence

ORD record
ord-6fbf7543b4cc4255a8c0a3746981431c
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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