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

HRID 44724Notes

Reaction equation

HRID 44724 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

Sodium azide (1.78 g, 27.4 mmol) was added to a solution of 3-(1-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)propyl methanesulfonate (prepared as described in Part D, 24.9 mmol) in dimethylformamide (100 mL). The reaction mixture was stirred for 2.5 d and additional sodium azide (160 mg) was added. The mixture was stirred an additional 1d, then was diluted with diethyl ether (250 mL) and washed with water (3×75 mL). The combined aqueous layers were back-extracted with diethyl ether (50 mL). 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. filtrationThe reaction mixture was filtered through CELITE
  2. filtrationfilter agent, which
  3. washwas rinsed afterwards with dichloromethane
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-604548f9ed284dceae9e0a347c35aaf9
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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