Ethanolamine → Benzyl 4-[(2hydroxyethyl)amino]piperidin-1-carboxylate

HRID 20216

Reaktionsgleichung

Reaktionsgleichung von HRID 20216
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[NH2:18][CH2:19][CH2:20][OH:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl.CO.C(O)(=O)C>[OH:21][CH2:20][CH2:19][NH:18][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1

Komponenten

8

Edukt 4

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 22137568Benzyl 4-[(2hydroxyethyl)amino]piperidin-1-carboxylateAusbeute 107,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of benzyl 4-oxopiperidin-1-carboxylate (7.0 g), 2-aminoethanol (2.8 g) and acetic acid (2.7 g) in 1,2-dichloroethane (150 mL)-methanol (10 mL) was stirred at room temperature for 3 hours, sodium triacetoxyborohydride (12.7 g) was added thereto, and the mixture was stirred at room temperature for 15 hours. A 1N sodium hydroxide solution was added to the reaction mixture, pH of the aqueous layer was adjusted to about 12, and then the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (9.0 g, quantitative) as a colorless oil.

Aufarbeitung

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-75db2ba6c6b64dc88b6623abe37c1296
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745623B2

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