N-[(1R,2R)-2-Hydroxycyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamide → N-[(1R)-2-Oxocyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamide

HRID 2367342

Reaktionsgleichung

Reaktionsgleichung von HRID 2367342
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([CH:11]1[O:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12]1)=[O:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([CH:11]1[O:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:12]1)=[O:10]

Komponenten

4

Edukt 2

HCID 58504652N-[(1R,2R)-2-Hydroxycyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamideHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 58504386N-[(1R)-2-Oxocyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamideAusbeute 14,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of N-[(1R,2R)-2-hydroxycyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamide (5.0 g, 15.7 mmol) and pyridinium chlorochromate (PCC) (4.06 g, 18.84 mmol) in CH2Cl2 (79 mL) was stirred at room temperature for 18 hours. The reaction mixture was filtered through a pad of silica gel and washed with EtOAc to get crude product (4.0 g). Purification was carried out on column chromatography (EtOAc—PE, from 2:1 to 2:0) to afford the title compound (0.7 g). LC-MS (ES) m/z=317 [M+H]+.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of silica gel
  2. washwashed with EtOAc
  3. customto get crude product (4.0 g)
  4. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-76d085be6b3449a9a8ca2f62c2a275c6
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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