Cyclohexene → HCID 15137746, compound

HRID 1086478Notes

Reaction equation

HRID 1086478 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C@H:8]([CH2:10][NH:11][C@@H:12]([CH3:31])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23]CC4C=CC=CC=4)[CH:21]=3)[NH:16][CH:15]=2)[OH:9])=[CH:4][CH:3]=1.C1CCCCC=1>C(O)C.[Pd]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C@H:8]([CH2:10][NH:11][C@@H:12]([CH3:31])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([OH:23])[CH:21]=3)[NH:16][CH:15]=2)[OH:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 15137744HCID 15137744, compound

Product 1

HCID 15137746HCID 15137746, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (R)-6-Amino-α-[[(1(S)-methyl-2-(5-benzyloxy-1H-indol-3-yl)ethyl)amino]methyl]-3-pyridinemethanol (619 mg) in 47 ml of absolute ethanol containing 7.9 g of cyclohexene and 198 mg of 10% Pd/C was heated at reflux under nitrogen for 3 hours. The reaction mixture was filtered and concentrated to dryness (510 mg). This residue was purified twice by preparative TLC (85:15:0.5 CH2Cl2 :MeOH:NH4OH) to give 224 mg of (R)-6-Amino-α-[[(1(S)-methyl-2-(5-hydroxy-1H-indol-3-yl)ethyl)amino]methyl]-3-pyridinemethanol.

Workup

  1. temperatureat reflux under nitrogen for 3 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated to dryness (510 mg)
  4. customThis residue was purified twice by preparative TLC (85:15:0.5 CH2Cl2 :MeOH:NH4OH)

Sources & evidence

ORD record
ord-0bcf67334ee84664958bc4c5322667df
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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