Cyclohexene → HCID 178511257, compound

HRID 2351830Notes

Reaction equation

HRID 2351830 reaction equation
C(=O)(O)O.C(OC(C1CC[N:13](C(N)=O)[CH2:12]C1)=O)C.N([C:23]1[CH:49]=[CH:48][C:26]([C:27]([NH:29][CH:30]([C:45]([OH:47])=[O:46])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:33]=2)=[O:28])=[CH:25][CH:24]=1)C(N)=N.C1CCCCC=1>CO.[Pd]>[NH2:13][CH2:12][C@H:23]1[CH2:24][CH2:25][C@H:26]([C:27]([NH:29][CH:30]([C:45]([OH:47])=[O:46])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:33]=2)=[O:28])[CH2:48][CH2:49]1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 178469238HCID 178469238, compound

Product 1

HCID 178511257HCID 178511257, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of the compound (III) (0.62 g), a palladium black (0.15 g), and cyclohexene (2 ml) in methanol (30 ml) was allowed to react under reflux of methanol for 1.5 hours. The reaction mixture was suction filtered while hot to remove the solid materials, followed by concentrating in vacuo. N-(trans-4-aminomethylcyclohexylcarbonyl)-3-phenoxy-DL-phenylalanine (0.30 g) was obtained in the form of a white powder.

Workup

  1. customto react
  2. filtrationfiltered while hot
  3. customto remove the solid materials
  4. concentrationby concentrating in vacuo

Sources & evidence

ORD record
ord-0ceaa7aead98490eb7cd01c739510e0c
Source dataset
uspto-grants-1989_10
Patent number
US04873253

Reaction notes

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