Triethylamine → HCID 59261033, compound

HRID 643550Notes

Reaction equation

HRID 643550 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[O:4][N:3]=1.[C:20]1(C)[C:21]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=1.[CH2:31](N(CC)CC)C>C1COCC1>[CH3:31][C:24]1[CH:25]=[CH:20][C:21]([S:26]([O:1][C:2]2[CH:6]=[C:5]([CH:7]3[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]3)[O:4][N:3]=2)(=[O:27])=[O:28])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 178451773HCID 178451773, compound

Product 1

HCID 59261033HCID 59261033, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cooled (0° C.) solution of tert-butyl 4-(3-hydroxyisoxazol-5-yl)piperidine-1-carboxylate (493 mg, 1.84 mmol) in 5 mL of THF was treated with toluenesulfonyl chloride (386 mg, 2.02 mmol) followed by triethylamine (295 μL, 2.12 mmol). The resulting mixture was warmed to rt and stirred for 2 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by MPLC (silica, 50% ethyl acetate/hexanes) to furnish tert-butyl 4-(3-{[(4-methylphenyl)sulfonyl]oxy}isoxazol-5-yl)piperidine-1-carboxylate. 1H NMR (500 MHz, CDCl3) δ 7.87 (d, J=8.5 Hz, 2H), 7.39 (d, J=8.0 Hz, 2H), 6.06 (s, 1H), 4.15 (br m, 2H), 2.88 (m, 3H), 2.49 (s, 3H), 2.00 (dd, J=13, 2.5 Hz, 2H), 1.62 (dq, J=4.5, 12.5 Hz, 2H), 1.49 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by MPLC (silica, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8c6c6270234641faa4f379dc7bf79d9d
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

Loading…