Benzyl Bromide → 2-benzyl 1-tert-butyl (2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate

HRID 1527328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527328
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[C@H:9]1[C:14]([O:16][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 14037017(2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Produkt 1

HCID 109252822-benzyl 1-tert-butyl (2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (2S,3S)-3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester [187039-57-2] (500 mg, 2.16 mmol) in MeOH (9.0 mL), cooled to 0° C., was added with stirring a solution of Cs2CO3 (704 mg, 2.162 mmol) in water (6.0 mL). The mixture was concentrated by rotary evaporation and the residue was suspended in DMF (17.0 mL). The suspension was cooled to 0° C., followed by addition of benzylbromide (0.514 mL, 4.32 mmol) and stirring overnight at RT. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organics were washed with aqueous NaHCO3 (2×) and water (2×), dried (Phase separator) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (EtOAc/c-hexane 2:3) to give the title compound as a white solid. MS (LC/MS): 665 [2M+Na]+, 266 [MH−tBu]+, 222 [MH−Boc]+; tR (HPLC conditions b): 4.18 min.

Aufarbeitung

  1. additionwas added
  2. concentrationThe mixture was concentrated by rotary evaporation
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in EtOAc
  6. washThe organics were washed with aqueous NaHCO3 (2×) and water (2×)
  7. customdried (Phase separator)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel (EtOAc/c-hexane 2:3)

Quellen und Nachweise

ORD-Eintrag
ord-ab1976539bb44edcade1e26e3eef3c1e
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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