Tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-chloro-2-fluorobenzoate → Tert-butyl 4-(bicyclo[3.1.0]hexan-3-ylmethoxy)-5-cyclopropyl-2-fluorobenzoate

HRID 1849820Notes

Reaction equation

HRID 1849820 reaction equation
[C:1]12([CH2:8][O:9][C:10]3[C:22](Cl)=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:12]([F:24])[CH:11]=3)C[CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2]2.[CH:25]12[CH2:30][CH:29]1CC(COC1C(Cl)=CC(C(OC(C)(C)C)=O)=C(F)C=1)C2>>[CH:5]12[CH2:4][CH:3]1[CH2:2][CH:1]([CH2:8][O:9][C:10]1[C:22]([CH:25]3[CH2:30][CH2:29]3)=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[C:12]([F:24])[CH:11]=1)[CH2:6]2

Participants

3

Reactant 2

HCID 86703665Tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-chloro-2-fluorobenzoateHCID 86703707Tert-butyl 4-(bicyclo[3.1.0]hexan-3-ylmethoxy)-5-chloro-2-fluorobenzoate

Product 1

HCID 86703706Tert-butyl 4-(bicyclo[3.1.0]hexan-3-ylmethoxy)-5-cyclopropyl-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 4-(bicyclo[3.1.0]hexan-3-ylmethoxy)-5-chloro-2-fluorobenzoate, the title compound was obtained as a colourless solid (1.20 g, 70% yield): 1H NMR (300 MHz, CDCl3) δ 7.35 (d, J=8.4 Hz, 1H), 6.43 (d, J=12.7 Hz, 1H), 3.78 (d, J=7.4 Hz, 2H), 2.88-2.74 (m, 2H), 2.16-2.07 (m, 1H), 1.98-1.89 (m, 1H), 1.55 (s, 9H), 1.50 (d, J=4.5 Hz, 1H), 1.46 (d, J=4.5 Hz, 1H), 1.30-1.25 (m, 2H), 0.88-0.82 (m, 2H), 0.58-0.53 (m, 2H), 0.09-0.05 (m, 1H); MS (ES+) m/z 369.1 (M+23).

Sources & evidence

ORD record
ord-29bcd15a3ee248598101ec45ec91f788
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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