Water → Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxobicyclo[4.1.0]heptan-1-yl)methoxy)benzoate

HRID 1849837Notes

Reaction equation

HRID 1849837 reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]34[CH2:30][CH:29]3[CH2:28][C:23]3(OCC[O:24]3)[CH2:22][CH2:21]4)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH2:2]1.O.FC(F)(F)C(O)=O>O1CCCC1.C(OCC)(=O)C>[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]34[CH2:30][CH:29]3[CH2:28][C:23](=[O:24])[CH2:22][CH2:21]4)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86703722Tert-butyl 5-cyclopropyl-2-fluoro-4-(spiro[bicyclo[4.1.0]heptane-3,2'-[1,3]dioxolan]-6-ylmethoxy)benzoate

Product 1

HCID 86703724Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxobicyclo[4.1.0]heptan-1-yl)methoxy)benzoateYield 90.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-cyclopropyl-2-fluoro-4-(spiro[bicyclo[4.1.0]heptane-3,2′-[1,3]dioxolan]-6-ylmethoxy)benzoate (0.61 g, 1.86 mmol) in tetrahydrofuran (2.0 mL) was added water (2.0 mL) followed by trifluoroacetic acid (0.75 g, 6.56 mmol). The reaction solution was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (20 mL), washed with a solution of aqueous sodium hydroxide (2.0 mL, 3 M). The organic layer was separated and concentrated in vacuo to afford the title compound as a colorless gum (0.63 g, quant.): 1H NMR (300 MHz, CDCl3) δ 7.36 (d, J=8.4 Hz, 1H), 6.43 (d, J=12.6 Hz, 1H), 3.91 (d, J=9.3 Hz, 1H), 3.71 (d, J=9.3 Hz, 1H), 2.72 (dd, J=18.4, 5.4 Hz, 1H), 2.56-2.32 (m, 4H), 2.20-2.07 (m, 2H), 1.99-1.92 (m, 1H), 1.53 (s, 9H), 1.21-0.79 (m, 5H), 0.70 (t, J=5.3 Hz, 1H), 0.63-0.58 (m, 2H); MS (ES+) m/z 397.2 (M+23).

Workup

  1. washwashed with a solution of aqueous sodium hydroxide (2.0 mL, 3 M)
  2. customThe organic layer was separated
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8404007d559e4fa191a4b1fd3cd90195
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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