Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate → 5-Cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzoic acid

HRID 1849794Notes

Reaction equation

HRID 1849794 reaction equation
C(C1(COC2C(C3CC3)=CC(C(OC(C)(C)C)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:32]1([C:35]2[C:36]([O:49][CH2:50][C:51]34[C:57]([F:59])([F:58])[CH:56]3[CH2:55][CH2:54][CH2:53][CH2:52]4)=[CH:37][C:38]([F:48])=[C:39]([CH:47]=2)[C:40]([O:42]C(C)(C)C)=[O:41])[CH2:34][CH2:33]1>>[CH:32]1([C:35]2[C:36]([O:49][CH2:50][C:51]34[C:57]([F:59])([F:58])[CH:56]3[CH2:55][CH2:54][CH2:53][CH2:52]4)=[CH:37][C:38]([F:48])=[C:39]([CH:47]=2)[C:40]([OH:42])=[O:41])[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 86703654Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoateHCID 86703677Tert-butyl 5-cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]-heptan-1-yl)methoxy)-2-fluorobenzoate

Product 1

HCID 867036765-Cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-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 5-cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]-heptan-1-yl)methoxy)-2-fluorobenzoate, the title compound was obtained (0.48 g, 80%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.53 (d, J=8.4 Hz, 1H), 6.51 (d, J=12.6 Hz, 1H), 4.00-3.90 (m, 2H), 1.97-1.71 (m, 5H), 1.47-1.22 (m, 5H), 0.95-0.86 (m, 2H), 0.69-0.61 (m, 2H).

Sources & evidence

ORD record
ord-3b344cbfdbdb447fa8806eeb94321291
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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