HCID 53790371, compound → HCID 54447355, compound

HRID 1734926Notes

Reaction equation

HRID 1734926 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C@@H:13]([O:24][CH2:25][O:26][CH3:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:7][C:6]=1[N+:28]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C@@H:13]([O:24][CH2:25][O:26][CH3:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:7][C:6]=1[NH2:28])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 53790371HCID 53790371, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54447355HCID 54447355, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.2 g (5.27 mmol) of (S)-2-t-butyl-5-(3-methoxymethyloxy-7-cyclohexyl-1-heptenyl)-1-nitrobenzene [prepared as described in step (iii) above] in 40 ml of ethanol was vigorously stirred in a stream of hydrogen for 6 hours in the presence of 1.5 g of 10% w/w palladium-on-charcoal. The catalyst was then filtered off and washed with ethanol. The filtrate and the washings were combined, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 9:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.16 g (yield 57%) of the title aniline derivative as an oil.

Workup

  1. filtrationThe catalyst was then filtered off
  2. washwashed with ethanol
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-98a187bbddc2402cb5318f2c064b2703
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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