Methyl chloroformate → Tert-butyl 4-{1-[(methoxycarbonyl)oxy]-3-(6-methylpyridin-2-yl)prop-2-yn-1-yl}piperidine-1-carboxylate

HRID 1895991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1895991
[OH:1][CH:2]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1.C(N(CC)CC)C.Cl[C:33]([O:35][CH3:36])=[O:34]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:36][O:35][C:33]([O:1][CH:2]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1)=[O:34]

Komponenten

6

Edukt 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 68725592Tert-butyl 4-[1-hydroxy-3-(6-methylpyridin-2-yl)prop-2-ynyl]piperidine-1-carboxylate

Produkt 1

HCID 68725060Tert-butyl 4-{1-[(methoxycarbonyl)oxy]-3-(6-methylpyridin-2-yl)prop-2-yn-1-yl}piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the Compound of Example 39 (50 mg, 0.15 mmol), triethylamine (65 μL, 0.45 mmol) and 4-dimethylaminopyridine (10 mg, 0.07 mmol) in 3 mL of CH2Cl2 cooled at 0-5° C., methyl chloroformate (23 μL, 0.30 mmol) was added dropwise. The reaction mixture was stirred at r.t. overnight. Afterwards, it was evaporated to dryness and purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 8:2 affording the title product (0.28 g) as a brown oil.

Aufarbeitung

  1. customAfterwards, it was evaporated to dryness
  2. custompurified by automated flash liquid chromatography (Horizon™-Biotage)
  3. washeluting with Petroleum Ether-EtOAc 8:2 affording the title product (0.28 g) as a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-17c29791f4a243a9bda0fb8fea311f67
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518916B2

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