Triethylamine → HCID 59261016, compound

HRID 643559Notes

Reaction equation

HRID 643559 reaction equation
[OH:1][C:2]1[C:6]2[CH:7]=[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[C:24]1(C)[C:25]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1.[CH2:35](N(CC)CC)C>C1COCC1>[CH3:35][C:28]1[CH:29]=[CH:24][C:25]([S:30]([O:1][C:2]2[C:6]3[CH:7]=[C:8]([CH:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]4)[CH:9]=[CH:10][C:5]=3[O:4][N:3]=2)(=[O:31])=[O:32])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 178451736HCID 178451736, compound

Product 1

HCID 59261016HCID 59261016, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cooled (0° C.) solution of tert-butyl 4-(3-hydroxy-1,2-benzisoxazol-5-yl)piperidine-1-carboxylate (286 mg, 0.898 mmol) in THF (5 mL) was treated with toluenesulfonyl chloride (188 mg, 0.988 mmol) followed by triethylamine (144 μL, 1.03 mmol). The reaction mixture was permitted to warm to rt and stir for 1.5 h. The reaction mixture was filtered, and the filtrate was concentrated. Purification by MPLC (silica, 50% ethyl acetate/hexanes) provided tert-butyl 4-(3-{[(4-methylphenyl)sulfonyl]oxy}-1,2-benzisoxazol-5-yl)piperidine-1-carboxylate. 1H NMR (500 MHz, CDCl3) δ 7.94 (d, J=8.5 Hz, 2H), 7.47 (s, 3H), 7.41 (d, J=8.0 Hz, 2H), 4.31 (br m, 2H), 2.85 (br m, 2H), 2.80 (tt, J=12, 3.5 Hz), 2.50 (s, 3H), 1.87 (br d, J=13 Hz, 2H), 1.64 (dq, J=4.5, 13 Hz, 2H), 1.52 (s, 9H). ESI-MS calc. for C24H28N2O6S: 472; Found: 473 (M+H).

Workup

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

Sources & evidence

ORD record
ord-7f1d79cad10f4015ba433e60eaa2c56f
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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