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Triethylamine → 2-(1,2-Diphenyl-ethyl)-morpholine-4-carboxylic acid benzyl ester

HRID 736038
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 736038
[C:1]1([CH:7]([CH:15]2[O:20][CH2:19][CH2:18][NH:17][CH2:16]2)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>ClCCl>[CH2:32]([O:31][C:29]([N:17]1[CH2:18][CH2:19][O:20][CH:15]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:16]1)=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 111498202-(1,2-Diphenyl-ethyl)-morpholine

Produkt 1

HCID 578486362-(1,2-Diphenyl-ethyl)-morpholine-4-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(1,2-Diphenyl-ethyl)-morpholine (2 g, 7.49 mmol) in dry dichloromethane (15 ml) at 0° C. under nitrogen atmosphere is added neat triethylamine (2.2 ml, 15.5 mmol, 2.07 equiv.) followed by the addition of neat benzyl chloroformate (1.61 ml, 11.23 mmol, 1.5 equiv.). The reaction is left to reach room temperature over 24 hours and then quenched by addition of a saturated bicarbonate (NaHCO3) aqueous solution. The resulting mixture is extracted with dichloromethane and the resulting organic phases are mixed, dried (MgSO4) and concentrated under reduced pressure to give an oil containing the four possible diastereoisomers (2.3 g, 78%). The diastereoisomers are separated using preparative HPLC, followed by each single enantiomer being resolved by preparative chiral HPLC.

Aufarbeitung

  1. waitThe reaction is left
  2. customquenched by addition of a saturated bicarbonate (NaHCO3) aqueous solution
  3. extractionThe resulting mixture is extracted with dichloromethane
  4. additionthe resulting organic phases are mixed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil
  8. additioncontaining the four possible diastereoisomers (2.3 g, 78%)
  9. customThe diastereoisomers are separated

Quellen und Nachweise

ORD-Eintrag
ord-e6c2da69357b4339931f4d4e73ec1a7f
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07595315B2

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