Tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-chloro-2-fluorobenzoate → Tert-butyl 5-cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]-heptan-1-yl)methoxy)-2-fluorobenzoate

HRID 1849854Notes

Reaction equation

HRID 1849854 reaction equation
[C:1]12(COC3C(Cl)=CC(C(OC(C)(C)C)=O)=C(F)C=3)[CH2:7][CH:6]1CCCC2.Cl[C:26]1[C:27]([O:40][CH2:41][C:42]23[C:48]([F:50])([F:49])[CH:47]2[CH2:46][CH2:45][CH2:44][CH2:43]3)=[CH:28][C:29]([F:39])=[C:30]([CH:38]=1)[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>>[CH:1]1([C:26]2[C:27]([O:40][CH2:41][C:42]34[C:48]([F:50])([F:49])[CH:47]3[CH2:46][CH2:45][CH2:44][CH2:43]4)=[CH:28][C:29]([F:39])=[C:30]([CH:38]=2)[C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 86703665Tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-chloro-2-fluorobenzoateHCID 86703734tert-butyl 5-chloro-4-(((1RS,6SR)-7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzoate

Product 1

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

Procedure

Following the procedure as described in Example 342 Step 4 and making variations as required to replace tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-chloro-2-fluorobenzoate with tert-butyl 5-chloro-4-(((1RS,6SR)-7,7- difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzoate (stereochemistry arbitrarily assigned), the title compound was obtained as a yellow oil (0.23 g, 81%): MS (ES+) m/z 341.0 (M−55).

Sources & evidence

ORD record
ord-a6f9b7e738f7428da51f5027a024fab2
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…