Imidazole → HCID 178455364, compound

HRID 1243163Notes

Reaction equation

HRID 1243163 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-butyldimethylsilyl chloride (19.63 g, 0.13 mol) (Avocardo Research Chemicals). The reaction mixture was stirred at room temperature for 1 day and then was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with 1N sodium hydroxide solution, water and brine, dried over magnesium sulfate, filtered and concentrated to give trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine. (Yield 7.62 g, 76.5%).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  3. washThe organic layer was washed with 1N sodium hydroxide solution, water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b69c894cac4b45f49c3c7acddad21308
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

Loading…