{[1-(3-Azidopropyl)cyclohexyl]oxy}(tert-butyl)dimethylsilane → HCID 57515400, compound

HRID 1469262Notes

Reaction equation

HRID 1469262 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[N+]=[N-]>[Pd].C(O)C>[Si:14]([O:13][C:7]1([CH2:6][CH2:5][CH2:4][NH2:1])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

4

Reactant 1

HCID 57457817{[1-(3-Azidopropyl)cyclohexyl]oxy}(tert-butyl)dimethylsilane

Product 1

HCID 57515400HCID 57515400, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The combined organic layers were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated to afford {[1-(3-azidopropyl)cyclohexyl]oxy}(tert-butyl)dimethylsilane (7.05 g, 95% over two steps) as a pale yellow oil. A mixture of the {[1-(3-azidopropyl)cyclohexyl]oxy}(tert-butyl)dimethylsilane (7.05 g, 23.7 mmol) and 5% palladium on carbon (0.71 g) in ethanol (100 mL) was hydrogenated at 30 psi (2.1×105 Pa) for 4 h on a Parr apparatus. The reaction mixture was filtered through CELITE filter agent, which was rinsed afterwards with dichloromethane, and the filtrate was concentrated to give 3-(1-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)propan-1-amine as a pale yellow oil (6.57 g, 102%) that contained a trace amount of solvent.

Workup

  1. washThe combined organic layers were washed with brine (100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford {[1-(3-azidopropyl)cyclohexyl]oxy}(tert-butyl)dimethylsilane (7.05 g, 95% over two steps) as a pale yellow oil
  6. filtrationThe reaction mixture was filtered through CELITE
  7. filtrationfilter agent, which
  8. washwas rinsed afterwards with dichloromethane
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b7b7eb4bbdf44010ae2f82cddd0025ea
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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