Diisopropylethylamine → HCID 58109248, compound

HRID 2037589Notes

Reaction equation

HRID 2037589 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([OH:8])[CH2:5][CH:6]=[CH2:7].CCN(C(C)C)C(C)C.Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.CCOCC>[CH2:5]([C:4]1([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[O:8][C:26](=[O:28])[NH:1][CH2:2][CH2:3]1)[CH:6]=[CH2:7]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 58109746HCID 58109746, compound

Product 1

HCID 58109248HCID 58109248, compoundYield 265.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1-amino-3-(4-fluorophenyl)hex-5-en-3-ol (53 mg, 0.25 mmol) and i-Pr2NEt (0.091 mL, 0.50 mmol) in CH2Cl2 (10 mL) was cooled in an ice bath and solid triphosgene (25 mg, 0.08 mmol) was added. The ice bath was allowed to melt and the mixture was stirred at rt for 6 h. The mixture was diluted with ether (80 mL), washed with 5% aq HCl (20 mL) and satd aq NaHCO3 (20 mL), and dried over MgSO4. Removal of the solvent afforded 6-allyl-6-(4-fluorophenyl)-1,3-oxazinan-2-one (50 mg, 84%) as an oil, which was used without further purification. LC-MS Method 1 tR=1.32 min, m/z=236.

Workup

  1. washwashed with 5% aq HCl (20 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-6367b43e9cc5402a8200542b5b6fc9e2
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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