1-Nitro-2-phenylethane → 2(S)-(2-Cyclohexylethyl)-5-(R)-(1-(R)-hydroxy-2-(S)-nitro-3-phenylpropyl)-morpholine-4-carboxylic acid tert-butyl ester

HRID 20370

Reaktionsgleichung

Reaktionsgleichung von HRID 20370
[C:1]1([CH2:7][CH2:8][N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([N:19]1[C@@H:24]([CH:25]=[O:26])[CH2:23][O:22][C@@H:21]([CH2:27][CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[C@@H:24]([C@@H:25]([OH:26])[C@@H:8]([N+:9]([O-:11])=[O:10])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:23][O:22][C@@H:21]([CH2:27][CH2:28][CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Komponenten

6

Edukt 3

HCID 802081-Nitro-2-phenylethaneHCID 2724141Tetrabutylammonium FluorideHCID 866153612-(S)-(2-Cyclohexylethyl)-5-(R)-formylmorpholine-4-carboxylic acid tert-butyl ester

Produkt 1

HCID 685582042(S)-(2-Cyclohexylethyl)-5-(R)-(1-(R)-hydroxy-2-(S)-nitro-3-phenylpropyl)-morpholine-4-carboxylic acid tert-butyl esterAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add 1-phenyl-2-nitroethane (91 mg, 0.61 mmol) to a solution of 2-(S)-(2-cyclohexylethyl)-5-(R)-formylmorpholine-4-carboxylic acid tert-butyl ester (164 mg, 0.50 mmol) in dry tetrahydrofuran (6 mL). Cool to 0° C. and add tetrabutylammonium fluoride (0.25 mL of a 1 M solution in tetrahydrofuran, 0.25 mmol) and refrigerate the solution overnight. Dilute with ethyl acetate, wash with cold saturated aqueous sodium chloride (50 mL), dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 2.5:97.5 ethyl acetate:dichloromethane) to give the desired compound as a white foam (152 mg, 63%).

Aufarbeitung

  1. customthe solution overnight
  2. washwash with cold saturated aqueous sodium chloride (50 mL)
  3. dry with materialdry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 2.5:97.5 ethyl acetate:dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-d78273dba6dc49e19ac8e515be59185f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745438B2

Verknüpfte Notizen

Wird geladen…