Triethylamine → 3-[(S)-1-(4-bromophenyl)ethyl]-6-isopropyl-6-(2-methylallyl)-1,3-oxazinan-2-one
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]([OH:21])([CH2:17][C:18]([CH3:20])=[CH2:19])[CH:14]([CH3:16])[CH3:15])[CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:11][CH2:12][C:13]([CH:14]([CH3:15])[CH3:16])([CH2:17][C:18]([CH3:20])=[CH2:19])[O:21][C:30]2=[O:32])[CH3:9])=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-{(S)-2-[1-(4-bromophenyl)-ethylamino]-ethyl}-2,5-dimethyl-hex-5-en-3-ol (6.4 g, 16.8 mmol) and triethylamine (5.34 g, 52 mmol) in CH2Cl2 (260 mL) was added triphosgene (2.52 g, 8.5 mmol) at 0° C. under N2, and the mixture was stirred at room temperature overnight. The reaction was quenched with water, and the mixture was extracted with CH2Cl2 (3×50 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by column chromatography to give two isomers of 3-[(S)-1-(4-bromophenyl)ethyl]-6-isopropyl-6-(2-methylallyl)-1,3-oxazinan-2-one.
Workup
- customThe reaction was quenched with water
- extractionthe mixture was extracted with CH2Cl2 (3×50 mL)
- washThe combined organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto afford the crude product, which
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-6c353cdc458f4b699e6c33fa884420ec
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846668B2
Reaction notes
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