Triethylamine → 6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-1,3-oxazinan-2-one

HRID 1096451Notes

Reaction equation

HRID 1096451 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]([CH:18]([CH3:20])[CH3:19])([OH:17])[CH2:14][CH:15]=[CH2:16])[CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:14]([C:13]1([CH:18]([CH3:20])[CH3:19])[O:17][C:29](=[O:31])[N:10]([C@H: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:15]=[CH2:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 596357281-((S)-1-(4-bromophenyl)ethylamino)-3-isopropylhex-5-en-3-ol

Product 1

HCID 596357496-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-1,3-oxazinan-2-oneYield 111.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-((S)-1-(4-bromophenyl)ethylamino)-3-isopropylhex-5-en-3-ol (802 mg, 2.366 mmol) and triethylamine (139 mg, 2.366 mmol) in CH2Cl2 (20 mL) was added triphosgene (348 mg, 1.18 mmol) at 0° C. under N2, and the mixture was stirred at rt overnight. The reaction mixture was quenched with water, and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated, and purified by column chromatography to give 6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-1,3-oxazinan-2-one (480 mg, 56% yield),

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-a6e27fcd8c604c7fa36d168253eadee2
Source dataset
uspto-grants-2012_03
Patent number
US08138178B2

Reaction notes

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