Diisopropylethylamine → 2-(Trimethylsilyl)ethyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1743265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743265
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[C:9](=O)([O:17]C1C=CC([N+]([O-])=O)=CC=1)[O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14].C(N(CC)C(C)C)(C)C>C1COCC1>[OH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:9]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:17])[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 4207714-PiperidinemethanolHCID 30861164-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

Produkt 1

HCID 113689482-(Trimethylsilyl)ethyl 4-(hydroxymethyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

10.5 g of 4-piperidinylmethanol were dissolved in 170 ml of THF. 25.8 g of 2-(trimethylsilyl)ethyl 4-nitrophenyl carbonate and 15.9 ml of N,N-diisopropylethylamine were successively added thereto. The mixture was stirred at room temperature for 1 h and then the solvent was removed in vacuo. The residue was taken up in 400 ml of ethyl acetate and washed once with 300 ml of 0.5 N HCl and twice with 250 ml of 1 N NaOH each time. The organic phase was dried with MgSO4, the solvent was removed in vacuo, and the residue was purified by chromatography on silica gel.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. washwashed once with 300 ml of 0.5 N HCl and twice with 250 ml of 1 N NaOH each time
  3. dry with materialThe organic phase was dried with MgSO4
  4. customthe solvent was removed in vacuo
  5. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e0f6906ac249442a966b213a3998dfcf
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07008957B2

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