t-Butyl 1-[9-[1-(tert-butoxycarbonyl)cyclopropyl]-5-oxononyl]-1-cyclopropanecarboxylate → 1-[9-(1-Carboxycyclopropyl)-5-oxononyl]-1-cyclopropanecarboxylic acid
Reaction equation
C([O:5][C:6]([C:8]1([CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:30])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]2([C:23]([O:25]C(C)(C)C)=[O:24])[CH2:22][CH2:21]2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C>C(O)=O>[C:23]([C:20]1([CH2:19][CH2:18][CH2:17][CH2:16][C:15](=[O:30])[CH2:14][CH2:13][CH2:12][CH2:11][C:8]2([C:6]([OH:7])=[O:5])[CH2:9][CH2:10]2)[CH2:22][CH2:21]1)([OH:25])=[O:24]Participants
3
Procedure
A solution of tert-butyl 1-[9-[1-(tert-butoxycarbonyl)cyclopropyl]-5-oxononyl]-1-cyclopropanecarboxylate (5.31 g, 12.6 mmol) in HCO2H (50 mL) was stirred for 3 h, evaporated in vacuo and coevaporated from toluene (3×25 mL) to give 1-[9-(1-carboxycyclopropyl)-5-oxononyl]-1-cyclopropanecarboxylic acid (3.89 g, 99%) as a white solid. An analytical sample was obtained after recrystallization from iPr2O/heptane. mp: 132-134° C. 1H NMR (CD3OD): δ=2.45 (t, J=6.9 Hz, 4H), 1.58-1.39 (m, 12H), 1.14 (dd, J=6.6, 3.7 Hz, 4H), 0.70 (dd, J=6.8, 3.9 Hz, 4H). 13C NMR (CD3OD): δ=214.4, 179.4 (2×), 43.5 (2×), 34.9 (2×), 28.5 (2×), 25.1 (2×), 24.2 (2×), 16.2 (4×). Anal. calcd for C17H26O5: C, 65.78; H; 8.44, found: C, 65.40; H, 8.37.
Workup
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-3cbb26fda5aa4f55822d7fb64833f722
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405226B2
Reaction notes
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