2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol → 3-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanenitrile
Reaction equation
O1CCCCC1OC1C=C(C23CCC(CCCCC#[N:27])(CC2)CO3)C=CC=1.[O:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[O:34][C:35]1[CH:36]=[C:37]([C:41]23[CH2:48][CH2:47][C:44]([CH2:49][CH2:50][CH2:51]CO)([CH2:45][CH2:46]2)[CH2:43][O:42]3)[CH:38]=[CH:39][CH:40]=1.O1CCCCC1OC1C=C(C23CCC(CCO)(CC2)CO3)C=CC=1>>[O:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[O:34][C:35]1[CH:36]=[C:37]([C:41]23[CH2:48][CH2:47][C:44]([CH2:49][CH2:50][C:51]#[N:27])([CH2:45][CH2:46]2)[CH2:43][O:42]3)[CH:38]=[CH:39][CH:40]=1Participants
Reactant 3
Product 1
Procedure
3-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanenitrile was prepared using a procedure analogous to 5-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pentanenitrile except that 4-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butan-1-ol was replaced with 2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol. The title compound was obtained (490 mg, 1.435 mmol, 87% yield) as a white solid. LCMS, [M+NH4]+=359.2. 1H NMR (500 MHz, CDCl3) δ 7.24 (t, J=8.0 Hz, 1H), 7.14-7.10 (m, 1H), 7.03-6.99 (m, 1H), 6.96 (ddd, J=8.2, 2.5, 0.8 Hz, 1H), 5.45 (t, J=3.2 Hz, 1H), 3.94 (ddd, J=11.3, 9.7, 3.2 Hz, 1H), 3.85 (s, 2H), 3.62 (m, 1H), 2.36-2.30 (m, 2H), 2.11-1.98 (m, 5H), 1.90-1.84 (m, 2H), 1.77-1.59 (m, 9H).
Workup
- custom3-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanenitrile was prepared
Sources & evidence
- ORD record
- ord-31db058eb562437a89aae7df85e3a3c4
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962660B2
Reaction notes
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