Triethylamine → 3-Ethynyl-1-(propane-2-sulfonyl)piperidine

HRID 1521935

Reaktionsgleichung

Reaktionsgleichung von HRID 1521935
[C:1]([CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1)#[CH:2].C(N(CC)CC)C.[CH3:16][CH:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18]>ClCCl>[C:1]([CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([S:19]([CH:17]([CH3:18])[CH3:16])(=[O:21])=[O:20])[CH2:4]1)#[CH:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 219638583-Ethynylpiperidine

Produkt 1

HCID 904115943-Ethynyl-1-(propane-2-sulfonyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Example 10A (500 mg, 4.58 mmol) in dichloromethane (10 mL) was added triethylamine (2.55 mL, 18.32 mmol) followed by propane-2-sulfonyl chloride (1.306 g, 9.16 mmol) and the mixture was stirred for 3 hours. The mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 30% ethyl acetate in hexane) afforded the title compound. LCMS: 216.2 (M+H-Boc)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (silica gel, 30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b8806f98aaf7449fae4f26dfec97ece2
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073922B2

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