3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole → HCID 90447582, compound

HRID 514866Notes

Reaction equation

HRID 514866 reaction equation
CC1(C)OI([C:11]([F:14])([F:13])[F:12])C2C1=CC=CC=2.[C:16]([O:19][C:20]1([CH2:33][CH:34]=[CH2:35])[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)(=[O:18])[CH3:17]>[Cu]I.CO>[C:16]([O:19][C:20]1(/[CH:33]=[CH:34]/[CH2:35][C:11]([F:14])([F:13])[F:12])[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:22][CH2:21]1)(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 160435723,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxoleHCID 90419021HCID 90419021, compound

Product 1

HCID 90447582HCID 90447582, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Procedure

A flame-dried vial equipped with a magnetic stir bar was charged with Togni reagent (2.0 g, 7.0 mmol) and CuI (34 mg, 0.35 mmol), and was sealed with a septum. The vial was evacuated and backfilled with N2 for three times. MeOH (8 mL) and tert-butyl 4-acetoxy-4-allylpiperidine-1-carboxylate (4.5 g, 14 mmol) were then added via syringe. The vial was kept at 80° C. for 2 h. The reaction mixture was concentrated in vacuo and the crude residue was purified by a standard method to afford the product (2.1 g). 1H NMR (400 MHz, CHLOROFORM-d) δ: 1.47 (s, 9 H), 1.66-1.77 (m, 2H), 2.00-2.07 (m, 3 H), 2.22 (d, J=13.43 Hz, 2 H), 2.85 (qdd, J=10.61, 10.61, 10.61, 7.25, 1.21 Hz, 2 H), 3.11 (t, J=11.82 Hz, 2 H), 3.81 (br. s., 2 H), 5.58 (dt, J=15.98, 7.19 Hz, 1 H), 6.05 (d, J=16.12 Hz, 1 H).

Workup

  1. customA flame-dried vial equipped with a magnetic stir bar
  2. customwas sealed with a septum
  3. customThe vial was evacuated
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe crude residue was purified by a standard method

Sources & evidence

ORD record
ord-fd857b52573f4aac9bc718fa6f202713
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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