HCID 131731865, compound → HCID 67291290, compound

HRID 74989Notes

Reaction equation

HRID 74989 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([O:10][CH3:11])[CH:5]1[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[NH2:1][CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([O:10][CH3:11])[CH:5]1[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

4

Reactant 1

HCID 131731865HCID 131731865, compound2×

Product 1

HCID 67291290HCID 67291290, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of racemic [1-Azido-3-methoxy-2-cyclohexanoxy]tert-butyl-dimethylsilane, 51g, (2.57 g; 6.3 mmol) in 20 mL of ethyl acetate was hydrogenated with Pd—C 10% (5 mole %; Degussa) at 45 PSI in a Parr hydrogenation apparatus for 1 h. The reaction mixture was filtered over a nylon and glass fiber filter and concentrated in vacuo to provide 2.32 g of the desired product 51h as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered over a nylon and glass fiber
  2. filtrationfilter
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5786e7f4d27d4924b1d1d5d541ddd1a1
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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