5-(1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)pentanoic acid → 4-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butanoic acid
Reaction equation
CC1SC(C23CCC(CC[CH2:23][CH2:24][C:25]([OH:27])=[O:26])(CC2)CO3)=C(C2C=CC=CC=2)N=1.ICC12CCC(C3SC(C)=NC=3C3C=CC=CC=3)(CC1)OC2.I[CH2:51][C:52]12[CH2:59][CH2:58][C:55]([C:60]3[CH:65]=[CH:64][CH:63]=[C:62]([O:66][CH:67]4[CH2:72][CH2:71][CH2:70][CH2:69][O:68]4)[CH:61]=3)([CH2:56][CH2:57]1)[O:54][CH2:53]2>>[O:68]1[CH2:69][CH2:70][CH2:71][CH2:72][CH:67]1[O:66][C:62]1[CH:61]=[C:60]([C:55]23[CH2:58][CH2:59][C:52]([CH2:51][CH2:23][CH2:24][C:25]([OH:27])=[O:26])([CH2:57][CH2:56]2)[CH2:53][O:54]3)[CH:65]=[CH:64][CH:63]=1Participants
Reactant 3
Product 1
Procedure
4-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butanoic acid was prepared using a procedure analogous to 5-(1-(2-methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)pentanoic acid except that 5-(4-(iodomethyl)-2-oxabicyclo[2.2.2]octan-1-yl)-2-methyl-4-phenylthiazole was replaced with 4-(iodomethyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octane. The title compound was obtained (0.88 g, 2.2 mmol, 95% yield) as a clear oil. LCMS, [M−H]+=373.1. 1H NMR (500 MHz, CDCl3) δ 7.23 (t, J=8.0 Hz, 1H), 7.17-7.10 (m, 1H), 7.05-6.99 (m, 1H), 6.95 (ddd, J=8.2, 2.5, 0.9 Hz, 1H), 5.45 (t, J=3.2 Hz, 1H), 3.94 (ddd, J=11.3, 9.9, 3.0 Hz, 1H), 3.84 (s, 2H), 3.67-3.58 (m, 1H), 2.36 (t, J=7.4 Hz, 2H), 2.11-1.99 (m, 5H), 1.91-1.82 (m, 2H), 1.77-1.54 (m, 9H), 1.26-1.16 (m, 2H).
Workup
- custom4-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butanoic acid was prepared
Sources & evidence
- ORD record
- ord-777e22dbdc2642fc9dd4ed7453f9bc7e
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962660B2
Reaction notes
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