Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate → 4-(Cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

HRID 1849799Notes

Reaction equation

HRID 1849799 reaction equation
C([C:3]1([CH2:13][O:14][C:15]2[C:27]([CH:28]3[CH2:30][CH2:29]3)=[CH:26][C:18]([C:19]([O:21]C(C)(C)C)=[O:20])=[C:17]([F:31])[CH:16]=2)[CH:10]2[CH2:11][CH:6]3[CH2:7]C(CC1C3)C2)#N.C1(COC2C(C3CC3)=CC(C(OC(C)(C)C)=O)=C(F)C=2)CCCC1>>[CH:3]1([CH2:13][O:14][C:15]2[C:27]([CH:28]3[CH2:29][CH2:30]3)=[CH:26][C:18]([C:19]([OH:21])=[O:20])=[C:17]([F:31])[CH:16]=2)[CH2:10][CH2:11][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 86703654Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoateHCID 86703683Tert-butyl 4-(cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoate

Product 1

HCID 867036214-(Cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Procedure

Following the procedure as described in Example 332 Step 6 and making non-critical variations to replace tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate with tert-butyl 4-(cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoate, the title compound was obtained as a colorless solid (3.0 g, 46%): 1H NMR (300 MHz, CDCl3) δ 7.27 (d, J=7.72 Hz, 1H), 6.85 (d, J=7.72 Hz, 1H), 3.92 (d, J=6.78 Hz, 2H), 2.38-2.22 (m, 1H), 2.05-1.89 (m, 1H), 1.83-1.67 (m, 2H), 1.64-1.44 (m, 4H), 1.41-1.26 (m, 2H), 0.89-0.79 (m, 2H), 0.60-0.52 (m, 2H).

Sources & evidence

ORD record
ord-d0d0b76903454d0ca2e0eda3f4b5a211
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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