Diazomethane → (1R)-1-(3-chlorophenyl)-2-[3-(3-methoxycarbonylmethoxyphenyl)cyclohexylamino]ethanol

HRID 1108775Notes

Reaction equation

HRID 1108775 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:28])[CH2:9][NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]3[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=3)[O:20][CH2:21][C:22]([OH:24])=[O:23])[CH2:12]2)[CH:5]=[CH:6][CH:7]=1.[N+](=[CH2:31])=[N-]>CO.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:28])[CH2:9][NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]3[CH:27]=[CH:26][CH:25]=[C:19]([O:20][CH2:21][C:22]([O:24][CH3:31])=[O:23])[CH:18]=3)[CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 11165592(2R)-(3-[3-[2-(3-chlorophenyl)-2-hydroxyethylamino]cyclohexyl]phenoxy) acetic acid

Product 1

HCID 54341635(1R)-1-(3-chlorophenyl)-2-[3-(3-methoxycarbonylmethoxyphenyl)cyclohexylamino]ethanolYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (2R)-(3-[3-[2-(3-chlorophenyl)-2-hydroxyethylamino]cyclohexyl]phenoxy)acetic acid (trans-H) obtained in Example 46 (1.0 g) in methanol (10 ml) there was added an excess of diazomethane in ether solution, and the mixture was stirred at room temperature for 30 minutes. After distilling off the solvent under reduced pressure, separation and purification by silica gel column chromatography (ethyl acetate:hexane=5:l) gave 0.91 g of (1R)-1-(3-chlorophenyl)-2-[3-(3-methoxycarbonylmethoxyphenyl)cyclohexylamino]ethanol (88% yield).

Workup

  1. distillationAfter distilling off the solvent
  2. customunder reduced pressure, separation and purification by silica gel column chromatography (ethyl acetate:hexane=5:l)

Sources & evidence

ORD record
ord-fe4389a367574f86969457ec3cd03058
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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