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Azide → (1R,2R,6S)-6-amino-2-[tert-butyl(dimethyl)silyl]oxy-2-methyl-cyclohexanol

HRID 74983
Notes
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Reaction equation

HRID 74983 reaction equation
[N-]=[N+]=[N-].[N:4]([C@H:7]1[CH2:12][CH2:11][CH2:10][C@:9]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])([CH3:13])[C@@H:8]1[OH:22])=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:4][C@H:7]1[CH2:12][CH2:11][CH2:10][C@:9]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])([CH3:13])[C@@H:8]1[OH:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 33558AzideHCID 86667433(1R,2R,3S)-3-azido-1-(tert-butyldimethylsilyloxy)-1-methylcyclo-hexan-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 68007680(1R,2R,6S)-6-amino-2-[tert-butyl(dimethyl)silyl]oxy-2-methyl-cyclohexanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 8857
Ethyl Acetate
Solvent

Procedure

A solution of azide, 50d, (0.25 g; 0.89 mmol) in 20 mL of ethyl acetate was hydrogenated with Degussa palladium (20 mole %) under 1 atmosphere of hydrogen overnight. The reaction mixture was filtered over celite and the celite was eluted with 2×10 mL of EtOAc. The filtrate was concentrated in vacuo to afford 230 mg of an oil that was used directly for the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. washthe celite was eluted with 2×10 mL of EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0d4cc5c0d6c04e548c25f4d3037b9914
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829007B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes