4-Methylmorpholine → HCID 178453954, Verbindung

HRID 421587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421587
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](O)=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C@@H:12]([CH2:15][OH:16])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 178453971HCID 178453971, Verbindung

Produkt 1

HCID 178453954HCID 178453954, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

cis-4-[(tert-Butoxy)carbonylamino]cyclohexane carboxylic acid (2.6 g, 10.68 mmol) was dissolved in THF (20 mL) and cooled to −10° C. (MeOH-ice). N-Methyl morpholine was added followed by isobutyl chloroformate (1.175 mL, 10.68 mmol). After 10 min, NaBH4 was added as a solid in one portion (1.213 g, 32.06 mmol). The reaction mixture was warmed to 0° C. and methanol was added dropwise (13.35 mL). After 30 min, the reaction was quenched with 5% aqueous KHSO4. The reaction was monitored by LC-MS until complete. The crude product was extracted with ethyl acetate and the combined extracts were dried over Na2SO4. A colorless oil was obtained and solidified slowly at room temperature. The product and purity were assessed by LC-MS and 1H NMR. No further purification was necessary. (quantitative yield) ES-MS (m/z) 230.

Aufarbeitung

  1. waitAfter 30 min
  2. customthe reaction was quenched with 5% aqueous KHSO4
  3. extractionThe crude product was extracted with ethyl acetate
  4. dry with materialthe combined extracts were dried over Na2SO4
  5. customA colorless oil was obtained
  6. customsolidified slowly at room temperature
  7. customNo further purification

Quellen und Nachweise

ORD-Eintrag
ord-d3817711c44b41d69f414bf9148f301e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101588B2

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