Hydrochloric Acid → HCID 178455365, compound

HRID 1243182Notes

Reaction equation

HRID 1243182 reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:23](Cl)(Cl)=[O:24].Cl>ClCCl>[C:1]([Si:5]([O:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([N:13]=[C:23]=[O:24])[CH2:11][CH2:12]1)([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 8471TriethylamineHCID 178455364HCID 178455364, compound

Product 1

HCID 178455365HCID 178455365, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine (1.0 g, 4.36 mmol) (from Example 3a supra) and triethylamine (3.04 mL, 21.8 mmol) (Burdick & Jackson) in dichloromethane (30 mL) at 0° C. was added phosgene (˜20% in toluene, 6.4 mL, 13.1 mmol) (Fluka) in one portion. The reaction mixture was stirred at 0° C. for 40 minutes, followed by addition of 0.5N aqueous hydrochloric acid (50 mL). The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate-hexanes (1:9) to give tert-butyl-(trans-4-isocyanato-cyclohexyloxy)-dimethyl-silane. (Yield 0.90 g, 81%).

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate-hexanes (1:9)

Sources & evidence

ORD record
ord-cd059f953a6049ca9d167ec48de11218
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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