Methyl chloroformate → (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(methoxycarbonylamino)ethoxy)ethyl)piperidine-1-carboxylate

HRID 451718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451718
[NH2:1][CH2:2][CH2:3][O:4][C@:5]([C@@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1)([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[CH3:6].CCN(C(C)C)C(C)C.Cl[C:37]([O:39][CH3:40])=[O:38]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:13][C:9]1[CH:8]=[C:7]([C@@:5]([C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)([O:4][CH2:3][CH2:2][NH:1][C:37]([O:39][CH3:40])=[O:38])[CH3:6])[CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 59201396(R)-tert-butyl 3-((R)-1-(2-aminoethoxy)-1-(3-chlorophenyl)ethyl)piperidine-1-carboxylate

Produkt 1

HCID 59201390(R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(methoxycarbonylamino)ethoxy)ethyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (R)-tert-butyl 3-((R)-1-(2-aminoethoxy)-1-(3-chlorophenyl)ethyl)piperidine-1-carboxylate (0.410 g, 1.07 mmol), DMAP (0.380 g), DIPEA (4 mL), and methyl chloroformate (0.960 g) in CH2Cl2 was stirred at rt for 20 h. After the reaction mixture was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC to afford (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(methoxycarbonylamino)ethoxy)ethyl)piperidine-1-carboxylate. MS ESI +ve m/z 465 (M+Na).

Aufarbeitung

  1. customAfter the reaction mixture was evaporated under reduced pressure
  2. customthe crude product was purified by reversed-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6851f8a5a841443db57902943158eda0
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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