Water → HCID 66856517, compound

HRID 2037497Notes

Reaction equation

HRID 2037497 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][CH2:11][CH2:12][C:13]([OH:20])([CH2:17][CH:18]=[CH2:19])[CH:14]([CH3:16])[CH3:15])[CH3:9])=[CH:4][CH:3]=1.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl.O>C(Cl)Cl>[CH2:17]([C:13]1([CH:14]([CH3:15])[CH3:16])[O:20][C:22](=[O:24])[N:10]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH3:9])[CH2:11][CH2:12]1)[CH:18]=[CH2:19]

Participants

5

Reactant 3

HCID 962WaterHCID 94429TriphosgeneHCID 66856884HCID 66856884, compound

Product 1

HCID 66856517HCID 66856517, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{2-[1-(4-bromo-phenyl)-ethylamino]-ethyl}-2-methyl-hex-5-en-3-ol (2.2 g, crude) and TEA (4 eq) in dried CH2Cl2 (60 mL) at 0° C. was added triphosgene (2.12 g, 7.12 mmol). The mixture was stirred at rt till the reaction was over. Water was added, and the layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic phase was washed with water, dried over Na2SO4, and condensed to give the crude product, which was purified by column to give 6-allyl-3-[1-(4-bromo-phenyl)-ethyl]-6-isopropyl-[1,3]oxazinan-2-one (500 mg, crude).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washThe combined organic phase was washed with water
  4. dry with materialdried over Na2SO4, and condensed
  5. customto give the crude product, which
  6. customwas purified by column

Sources & evidence

ORD record
ord-3b6dc05d7ff14e0c922db8e6c619aa8d
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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