Triethylamine → Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 220829

Reaktionsgleichung

Reaktionsgleichung von HRID 220829
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[CH2:16]([O:23][C:24]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 4207714-Piperidinemethanol

Produkt 1

HCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylateAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Piperidinemethanol (5.0 g, 43 mmol) was dissolved in dichloromethane (100 ml) and triethylamine (12 ml, 86 mmol) at 0° C. Benzylchloroformate (6.8 ml, 47.3 mmol) was added and the mixture was stirred for 20 h at room temperature then solvents were removed in vacuo. The residue was redissolved in EtOAc, washed with 1M KHSO4, water then brine, dried and concentrated in vacuo to yield the title compound (8.33 g, 77%).

Aufarbeitung

  1. customat 0° C
  2. customsolvents were removed in vacuo
  3. dissolutionThe residue was redissolved in EtOAc
  4. washwashed with 1M KHSO4, water
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-35cccfc29ede41b78bef529063086ea2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202858B2

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