Triethylamine → (R)-4-[3-(4-Butylidenepiperidin-1-yl)-2-methylpropyl]-6-methyl-4H-benzo[1,4]oxazin-3-one

HRID 2102604Notes

Reaction equation

HRID 2102604 reaction equation
I[CH2:2][C@@H:3]([CH3:17])[CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:16].CCN(CC)CC.[CH:25](=[C:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH2:26][CH2:27][CH3:28]>C(Cl)Cl.CC(C)=O.CO>[CH:25](=[C:29]1[CH2:34][CH2:33][N:32]([CH2:2][C@@H:3]([CH3:17])[CH2:4][N:5]2[C:10]3[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=3[O:8][CH2:7][C:6]2=[O:16])[CH2:31][CH2:30]1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 149666594-ButylidenepiperidineHCID 68908548(S)-4-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 68911101(R)-4-[3-(4-Butylidenepiperidin-1-yl)-2-methylpropyl]-6-methyl-4H-benzo[1,4]oxazin-3-oneYield 62.7%

Reagents, catalysts & solvents 1

HCID 21584259acetone MeOH DCMSolvent

Procedure

Crude (S)-4-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one (0.34 g), Et3N (0.5 mL) and 4-butylidenepiperidine (0.17 g, 1.2 mmol) were reacted according to GP17. Flash CC (SiO2; CH2Cl2/acetone/MeOH 90:7:3) gave the title compound (0.22 g, 58%). 1H NMR (CD3OD) δ 7.01 (s, 1H), 6.86 (d, J=8.0 Hz, 1H), 6.82 (dm, J=8.0 Hz, 1H), 5.12 (t, J=7.2 Hz, 1H), 4.52 (ABq, J=14.8, 20.8 Hz, 2H), 4.03 (dd, J=5.6, 14.4 Hz, 1H), 3.91 (dd, J=8.0, 14.4 Hz, 1H), 2.48-2.34 (m, 2H), 2.33-2.11 (m, 8H), 2.31 (s, 3H), 1.96 (q, J=7.2 Hz, 2H), 1.34 (m, 2H), 0.91-0.86 (m, 6H); 13C NMR (CD3OD) δ 165.9, 143.9, 136.0, 132.4, 128.3, 124.3, 122.4, 116.6, 116.2, 67.4, 63.6, 56.3, 55.4, 45.0, 28.92, 28.85, 28.0, 23.0, 20.0, 15.9, 12.8.

Sources & evidence

ORD record
ord-98a528cfdf2343d5aba12313bbd5df20
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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