HCID 58822102, compound → HCID 68905445, compound

HRID 546479Notes

Reaction equation

HRID 546479 reaction equation
[N:1]([C@@H:4]1[C@@H:9]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:7][C@@H:6]([CH2:18][O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:5]1)=[N+]=[N-].[H][H]>CO.[Pd]>[C:14]([O:13][C:11]([NH:10][C@H:9]1[CH2:8][CH2:7][C@@H:6]([CH2:18][O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:5][C@@H:4]1[NH2:1])=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 58822102HCID 58822102, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68905445HCID 68905445, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(1R,3S,4S)-3-Azido-4-(N-tert-butoxycarbonyl-amino)-1-(tert-butyldiphenylsilyloxymethyl)cyclohexane (2.59 g) was dissolved in methanol (50 ml), and 10% palladium on carbon (200 mg) was added to stir the mixture for 20 hours in a hydrogen atmosphere. After the catalyst was removed by filtration, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:20→1:10) to obtain (1S,2S,4R)—N1-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1,2-cyclohexanediamine (1.66 g) as a pale yellow oil.

Workup

  1. customAfter the catalyst was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:20→1:10)

Sources & evidence

ORD record
ord-b4694e2d192a4c578c83d51d45df3583
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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