HCID 54486000, compound → HCID 54528553, compound

HRID 977871Notes

Reaction equation

HRID 977871 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C@@H:13]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:7][C:6]=1[N+:29]([O-:31])=[O:30])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)C.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C@@H:13]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:7][C:6]=1[N+:29]([O-:31])=[O:30])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 54486000HCID 54486000, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54528553HCID 54528553, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.75 g (6.17 mmol) of (S)-2-t-butyl-5-(3-t-butyldimethylsilyloxy-4-cyclohexyl-1-butenyl)-1-nitrobenzene [prepared as described in step (v) above] in 30 ml of diethyl ether was vigorously stirred for 20 minutes at 0° C. in a stream of hydrogen and in the presence of 303 mg of 10% w/w palladium-on-charcoal. The reaction mixture was then worked up in a similar manner to that described in step (iii) above, to give 2.65 g (yield 96%) of the title nitrobenzene derivative as a colorless oil.

Sources & evidence

ORD record
ord-c4319d2b69bd4cf1b1155c007b78cde6
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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