Triethylamine → HCID 69322750, compound

HRID 1350148Notes

Reaction equation

HRID 1350148 reaction equation
[CH2:1]([N:4]1[C:17]2[C:8](=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[C:12]([O:18][CH:19]([CH3:21])[CH3:20])[CH:11]=[C:10]3[C:22]([F:25])([F:24])[F:23])[O:7][CH2:6][C@H:5]1[CH2:26][CH3:27])[CH:2]=[CH2:3].CCN(CC)CC>CCOC(C)=O.[Pd]>[CH2:26]([C@@H:5]1[CH2:6][O:7][C:8]2=[C:9]3[C:14](=[CH:15][CH:16]=[C:17]2[N:4]1[CH2:1][CH2:2][CH3:3])[N:13]=[C:12]([O:18][CH:19]([CH3:20])[CH3:21])[CH:11]=[C:10]3[C:22]([F:23])([F:25])[F:24])[CH3:27]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 69320996HCID 69320996, compound

Product 1

HCID 69322750HCID 69322750, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3R)-4-allyl-3-ethyl-3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (0.24 g, 0.63 mmol) and 0.1 mL Et3N in 3 mL EtOAc was added 10% Pd on carbon (0.08 g) and the mixture was vigorously stirred under H2 atmosphere for 1 h. The reaction mixture was filtered through Celite and concentrated to give 0.23 g (96% yield) of (3R)-3-ethyl-3,4-dihydro-8-isopropoxy-4-propyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline, a yellow oil. Rf0.7 (9:1 hexane:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.41 (d, 1H, J=9.1), 7.22 (d, 1H, J=9.1), 7.17 (s, 1H), 5.47 (septet, 1H, J=6.2), 4.30 (dd, ABX, 1H, J=10.5, 1.6), 3.86 (dd, ABX, 1H, J=10.5, 2.5), 3.47–3.35 (m, 1H), 3.23–3.11 (m, 2H), 1.70–1.55 (m, 4H), 1.38 (d, 3H, J=6.2), 1.37 (d, 3H, J=6.2), 1.02–0.91 (m, 6H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-68ac764ef6074f2b864fd62307fc1e26
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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