Water → HCID 69320996, compound

HRID 1350147Notes

Reaction equation

HRID 1350147 reaction equation
[CH2:1]([C@@H:3]1[CH2:24][O:23][C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[NH:4]1)[N:11]=[C:10]([O:15][CH:16]([CH3:18])[CH3:17])[CH:9]=[C:8]3[C:19]([F:22])([F:21])[F:20])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[CH:32]=[CH2:33].O>CN(C=O)C.CCCCCC.CCOC(C)=O>[CH2:33]([N:4]1[C:5]2[C:6](=[C:7]3[C:12](=[CH:13][CH:14]=2)[N:11]=[C:10]([O:15][CH:16]([CH3:18])[CH3:17])[CH:9]=[C:8]3[C:19]([F:21])([F:22])[F:20])[O:23][CH2:24][C@H:3]1[CH2:1][CH3:2])[CH:32]=[CH2:31]

Participants

8

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 69319657HCID 69319657, compound

Product 1

HCID 69320996HCID 69320996, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of (3R)-3-ethyl-3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (0.250 g, 0.734 mmol) and K2CO3 (0.507 g, 3.67 mmol) in 3 mL DMF was added allyl bromide (0.636 mL, 7.34 mmol) and the reaction mixture was heated to 50° C. for 4 h. The reaction mixture was poured into 40 mL water and extracted with EtOAc (2×30 mL). The extracts were washed with 40 mL each water and brine, dried over MgSO4, filtered and concentrated to a yellow oil. Column chromatography (5–10% EtOAc in hexane gradient) afforded 0.24 g (86% yield) of (3R)-4-allyl-3-ethyl-3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline, a yellow oil. Rf0.6 (9:1 hexane:EtOAc); 1H NMR (400 MHz, CDCl3) δ7.41 (d, 1H, J=9.0), 7.21 (d, 1H, J=9.0), 7.18 (s, 1H), 5.96–5.85 (m, 1H), 5.47 (septet, 1H, J=6.1), 5.25 (dd, ABX, 1H, J=17.1, 1.1), 5.20 (d, 1H, J=10.1), 4.31 (dd, ABX, 1H, J=10.7, 2.2), 4.03 (dd, ABX, 1H, J=16.8, 5.0), 3.95–3.89 (m, 2H), 3.27–3.22 (m, 1H), 1.69–1.59 (m, 2H), 1.38 (d, 3H, J=6.1), 1.37 (d, 3H, J=6.1), 0.97 (t, 3H, J=7.5).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe extracts were washed with 40 mL each water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil

Sources & evidence

ORD record
ord-02edf78815854e13b0d99747a06ea816
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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