Tert-butyl 5-chloro-4-((1-cyanocyclohexyl)methoxy)-2-fluorobenzoate → Methyl 5-cyclopropyl-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzoate

HRID 1849918Notes

Reaction equation

HRID 1849918 reaction equation
ClC1C(OCC2(C#N)CCCCC2)=C[C:5](F)=[C:6]([CH:14]=1)C(OC(C)(C)C)=O.Cl[C:27]1[C:28]([O:38][CH:39]2[CH2:46][CH2:45][C:42]3([CH2:44][CH2:43]3)[CH2:41][CH2:40]2)=[CH:29][C:30]([F:37])=[C:31]([CH:36]=1)[C:32]([O:34][CH3:35])=[O:33]>>[CH:14]1([C:27]2[C:28]([O:38][CH:39]3[CH2:46][CH2:45][C:42]4([CH2:44][CH2:43]4)[CH2:41][CH2:40]3)=[CH:29][C:30]([F:37])=[C:31]([CH:36]=2)[C:32]([O:34][CH3:35])=[O:33])[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 86703716Tert-butyl 5-chloro-4-((1-cyanocyclohexyl)methoxy)-2-fluorobenzoateHCID 86703797Methyl 5-chloro-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzoate

Product 1

HCID 86703798Methyl 5-cyclopropyl-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzoate

Procedure

Following the procedure as described in Example 374 Step 3 and making non-critical variations to replace tert-butyl 5-chloro-4-((1-cyanocyclohexyl)methoxy)-2-fluorobenzoate with methyl 5-chloro-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzoate, the title compound was obtained as a colorless syrup (0.389 g, 72% yield): 1H NMR (300 MHz, CDCl3) δ 7.42 (d, J=8.5 Hz, 1H), 6.56 (d, J=13.0 Hz, 1H), 4.46-4.39 (m, 1H), 3.86 (s, 3H), 2.10-2.01 (m, 1H), 1.99-1.90 (m, 2H), 1.86-1.76 (m, 2H), 1.54-1.24 (m, 4H), 0.96-0.84 (m, 3H), 0.66-0.60 (m, 2H), 0.32-0.26 (m, 4H); MS (ES+) m/z 287.05 (M−31).

Sources & evidence

ORD record
ord-405840b70dfe4365a6154056509ecd3b
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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