Triethylamine → HCID 66856865, compound

HRID 2037475Notes

Reaction equation

[CH2:1]([NH:9][CH2:10][CH2:11][C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:16])[CH2:13][CH:14]=[CH2:15])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(CC)CC.Cl[C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:13]([C:12]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:16][C:31](=[O:33])[N:9]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][CH2:11]1)[CH:14]=[CH2:15]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 1-phenethylamino-3-phenyl-hex-5-en-3-ol (120 mg, 0.41 mmol) and Et3N (0.5 mL) in anhydrous CH2Cl2 (5 mL) was added triphosgene (40 mg, 0.134 mmol) in portions at 0° C. under N2. Then the solution was refluxing at 80-90° C. overnight. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC to afford 6-allyl-3-phenethyl-6-phenyl-[1,3]oxazinan-2-one (234 mg, yield: 19%). 1H NMR (CDCl3): 2.07-2.17 (m, 2H), 2.44-2.60 (m, 2H), 2.62-2.84 (m, 4H), 3.25 (m, 1H), 3.52 (m, 1H), 3.09 (m, 1H), 5.04 (m, 2H), 5.47-5.58 (m, 1H), 6.94 (m, 2H), 7.10 (m, 3H), 7.27 (m, 3H), 7.31 (m, 2H).

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by preparative TLC

Sources & evidence

ORD record: ord-7d732665487a4e34830f1310548a56b6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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