Triethylamine → (R)-4-[3-(3-Butyl-8-azabicyclo[3.2.1]oct-8-yl)-2-methylpropyl]-6-methyl-4H-benzo[1,4]oxazin-3-one

HRID 2103266Notes

Reaction equation

HRID 2103266 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.[CH2:25]([CH:29]1[CH2:35][CH:34]2[NH:36][CH:31]([CH2:32][CH2:33]2)[CH2:30]1)[CH2:26][CH2:27][CH3:28]>C(Cl)Cl.CC(O)C>[CH2:25]([CH:29]1[CH2:30][CH:31]2[N:36]([CH2:2][C@@H:3]([CH3:17])[CH2:4][N:5]3[C:10]4[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=4[O:8][CH2:7][C:6]3=[O:16])[CH:34]([CH2:33][CH2:32]2)[CH2:35]1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 689079663-Butyl-8-azabicyclo[3,2,1]octaneHCID 68908548(S)-4-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 68912686(R)-4-[3-(3-Butyl-8-azabicyclo[3.2.1]oct-8-yl)-2-methylpropyl]-6-methyl-4H-benzo[1,4]oxazin-3-oneYield 62.6%

Reagents, catalysts & solvents 1

HCID 21966342Isopropanol methylene chlorideSolvent

Procedure

Crude (S)-4-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one (0.19 g, 0.54 mmol), Et3N (0.5 mL) and 3-butyl-8-azabicyclo[3.2.1]octane (0.10 g, 0.61 mmol) were reacted according to GP17. Flash CC (SiO2; CH2Cl2/i-PrOH 92:8) gave the title compound (0.13 g, 62%). 1H NMR (CD3OD) δ 7.05 (s, 1H), 6.86 (d, J=8.4 Hz, 1H), 6.81 (dm, J=8.4 Hz, 1H), 4.52 (ABq J=14.8, 24.8 Hz, 2H), 4.05 (dd, J=5.6, 14.0 Hz, 1H), 3.94 (dd, J=8.8, 14.0 Hz, 1H), 3.05-3.16 (m, 2H), 2.35-2.14 (m, 2H), 2.31 (s, 3H), 2.05-1.78 (m, 3H), 1.63-1.40 (m, 5H), 1.36-1.12 (m, 5H), 0.99 (d, J=6.4 Hz, 3H), 0.90 (t, J=6.8 Hz, 3H); 13C NMR (CD3OD) δ 167.4, 144.9, 133.7, 129.2, 125.6, 117.7, 117.3, 68.5, 63.2 (br), 62.5(br), 56.0(Br), 43.3, 37.8 (br), 31.3, 30.5, 30.0, 28.3, 26.7, 26.4, 23.7, 21.0, 16.8, 14.2.

Sources & evidence

ORD record
ord-8c6f62a507fa4b9b87528738980ad420
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

Loading…