Tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-chloro-2-fluorobenzoate → Tert-butyl 5-cyclopropyl-2-fluoro-4-(spiro[bicyclo[4.1.0]heptane-3,2'-[1,3]dioxolan]-6-ylmethoxy)benzoate

HRID 1849836Notes

Reaction equation

HRID 1849836 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[CH2:52][CH:51]2[CH2:50][C:45]2([O:49][CH2:48][CH2:47][O:46]2)[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[CH2:52][CH:51]3[CH2:50][C:45]3([O:46][CH2:47][CH2:48][O:49]3)[CH2:44][CH2:43]4)=[CH:28][C:29]([F:39])=[C:30]([CH:38]=2)[C:31]([O:33][C:34]([CH3:37])([CH3:36])[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 86703723Tert-butyl 5-chloro-2-fluoro-4-(spiro[bicyclo[4.1.0]heptane-3,2'-[1,3]dioxolan]-6-ylmethoxy)benzoate

Product 1

HCID 86703722Tert-butyl 5-cyclopropyl-2-fluoro-4-(spiro[bicyclo[4.1.0]heptane-3,2'-[1,3]dioxolan]-6-ylmethoxy)benzoate

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 of tert-butyl 5-chloro-2-fluoro-4-(spiro[bicyclo[4.1.0]heptane-3,2′-[1,3]dioxolan]-6-ylmethoxy)benzoate, the title compound was obtained as a colorless solid (1.30 g, 93%): 1H NMR (300 MHz, CDCl3) δ 7.35 (d, J=8.3 Hz, 1H), 6.42 (d, J=12.7 Hz, 1H), 3.95-3.86 (m, 4H), 3.84-3.70 (m, 2H), 2.22-1.98 (m, 4H), 1.82-1.72 (m, 2H), 1.64-1.57 (m, 2H), 1.56 (s, 9H), 1.49-1.35 (m, 2H), 1.11-1.04 (m, 1H), 0.80-0.75 (m, 11H), 0.65-0.60 (m, 1H), 0.56 (t, J=5.3 Hz, 1H); MS (ES+) m/z 419.2 (M+1).

Sources & evidence

ORD record
ord-85b4c4c5ff244f0c84ff35e08d7bfa1b
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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