Benzyl chloroformate → HCID 22872576, compound

HRID 1779996Notes

Reaction equation

HRID 1779996 reaction equation
[CH3:1][C@H:2]([C@@H:5]([CH3:12])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH2:3][NH2:4].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C(=O)([O-])O.[K+]>O1CCOCC1.O>[CH3:1][C@H:2]([C@@H:5]([CH3:12])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH3:11])[CH2:3][NH:4][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516893Potassium BicarbonateHCID 22872574HCID 22872574, compound

Product 1

HCID 22872576HCID 22872576, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Separate solutions of 2(R),3(S),7-trimethyl-1-amino-6-octene (0.87 g, 5.2 mmol) in 8 mL of dioxane, and benzyl chloroformate (0.86 mL, ~6 mmol) in 8 mL of dioxane were added dropwise simultaneously to a stirred solution of 1.05 g (10.5 mmol) of potassium hydrogen carbonate in 20 mL of water at 0° C. After the additions, the mixture was stirred 8 hrs at room temperature. Most of the volatile solvents were removed in vacuo. The remaining reaction mixture was extracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate. Solvent removal gave the crude product which was purified on silica gel using 10% ethyl acetate in hexane as solvent to give 1.4 g of the desired carbamate as a colorless oil.

Workup

  1. customMost of the volatile solvents were removed in vacuo
  2. customThe remaining reaction mixture
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  5. customSolvent removal
  6. customgave the crude product which
  7. customwas purified on silica gel using 10% ethyl acetate in hexane as solvent

Sources & evidence

ORD record
ord-a11c6044ff444d80b4184bd01493c194
Source dataset
uspto-grants-1997_05
Patent number
US05629322

Reaction notes

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