Triphenylphosphine → 2-cyclopentyl-6-methoxybenzo[d]isoxazol-3(2H)-one

HRID 404974Notes

Reaction equation

HRID 404974 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH:13]1([N:18]([OH:30])[C:19](=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2O)[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:13]1([N:18]2[C:19](=[O:29])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[O:30]2)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 50994754N-cyclopentyl-N,2-dihydroxy-4-methoxybenzamide

Product 1

HCID 509947552-cyclopentyl-6-methoxybenzo[d]isoxazol-3(2H)-oneYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate was added dropwise to a cooled solution of N-cyclopentyl-N, 2-dihydroxy-4-methoxybenzamide (0.71 g, 2.8 mmol), and triphenylphosphine (0.89 g, 3.4 mmol) in tetrahydrofuran (30 mL) The reaction mixture was warmed to room temperature and quenched with 1:1 CH3OH:CH3CO2H (0.2 mL). Removal of the solvent in vacuo followed by chromatographic separation on silica gel afforded 2-cyclopentyl-6-methoxybenzo[d]isoxazol-3(2H)-one as pale yellow solid (0.3 g, 46%). 1H NMR (300 MHz, DMSO-d6): δ 7.67 (d, 1H, J=8.7 Hz), 6.78 (d, 1H, J=8.6 Hz), 6.32 (s, 1H), 4.35-4.33 (m, 1H), 3.84 (s, 3H), 1.89-1.68 (m, 8H). LC-MS (ESI) Calcd for C13H15NO3 [M+H]+: 234.10. Found: 233.90.

Workup

  1. customquenched with 1:1 CH3OH
  2. customRemoval of the solvent in vacuo
  3. customfollowed by chromatographic separation on silica gel

Sources & evidence

ORD record
ord-45490dd099bf4665833418110f4b09bf
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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