Imidazole → HCID 178455364, compound

HRID 2216997Notes

Reaction equation

HRID 2216997 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>ClCCl>[C:17]([Si:14]([CH3:16])([CH3:15])[O:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([NH2:1])[CH2:3][CH2:4]1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178511715HCID 178511715, compound

Product 1

HCID 178455364HCID 178455364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-4-aminocyclohexanol (5.0 g, 43.4 mmol) (TCl US) in dichloromethane (100 mL) was added imidazole (14.78 g, 0.22 mol) (Aldrich) and tert-butyidimethylsilyl chloride (19.63 g, 0.13 mol) (Avocardo Research Chemicals). The reaction mixture was stirred at room temperature for 1 day. It was concentrated under reduced pressure, and the residue was diluted with ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with 1 N sodium hydroxide solution, water and brine, dried (MgSO4), filtered and concentrated to give crude trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine which was used in the next step without further purification. (Yield 7.62 g, 76.5%).

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (100 mL) and water (100 mL)
  3. washThe organic layer was washed with 1 N sodium hydroxide solution, water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cf0b544f9bb64567845fe4bc87ffc5fd
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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