HCID 86590033, compound → HCID 178484010, compound

HRID 967124Notes

Reaction equation

HRID 967124 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:9][CH:10]1[CH2:15][CH2:14][CH:13](/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][Br:21])[CH2:12][CH2:11]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pt](=O)=O.[Pt]>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Br:21])[CH2:12][CH2:11]1)[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 86590033HCID 86590033, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178484010HCID 178484010, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

1.15 g (3.07 mmol) trans-E/Z-[4-(5-bromo-pent-1-enyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester dissolved in 15 ml of ethanol were added to a suspension of 300 mg platinum dioxide freshly reduced to platinum by hydrogenation immediately prior to use. Hydrogenation was then continued at ambient pressure until 95% of the calculated amount of hydrogen had been consumed. Then, the reaction mixture was filtered over celite and evaporated giving 0.950 g (82%) trans-[4-(5-bromo-pentyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS: 375 (M+, 1Br).

Workup

  1. customhad been consumed
  2. filtrationThen, the reaction mixture was filtered over celite
  3. customevaporated

Sources & evidence

ORD record
ord-a86e33967b8749e0a64670a4404a2f93
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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