Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate → 4-(Bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

HRID 1849784Notes

Reaction equation

HRID 1849784 reaction equation
[C:1]([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]3CC(C[CH:4]1[CH2:5]3)C2)#N.C12(COC3C(C4CC4)=CC(C(OC(C)(C)C)=O)=C(F)C=3)CC1CCCC2>>[C:3]12([CH2:13][O:14][C:15]3[C:27]([CH:28]4[CH2:30][CH2:29]4)=[CH:26][C:18]([C:19]([OH:21])=[O:20])=[C:17]([F:31])[CH:16]=3)[CH2:1][CH:4]1[CH2:5][CH2:6][CH2:11][CH2:10]2

Participants

3

Reactant 2

HCID 86703654Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoateHCID 86703666Tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoate

Product 1

HCID 867036674-(Bicyclo[4.1.0]heptan-1-ylmethoxy)-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-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoate, the title compound was obtained as a colorless solid (0.30 g, 37%): 1H NMR (300 MHz, CDCl3) δ 7.37 (d, J=8.5 Hz, 1H), 6.42 (d, J=12.8 Hz, 1H), 3.61 (d, J=9.1 Hz, 1H), 3.78 (d, J=9.1 Hz, 1H), 1.96-1.52 (m, 7H), 0.92-0.82 (m, 4H), 0.67-0.61 (m, 4H), 0.38-0.33 (m, 1H).

Sources & evidence

ORD record
ord-5792188b953c499b90157e79503d6bca
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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