Diisopropylethylamine → 1-(9H-fluoren-9-yl)methyl 5-tert-butyl hexahydropyrrolo[3,4-b]pyrrole-1,5-dicarboxylate

HRID 57604

Reaktionsgleichung

Reaktionsgleichung von HRID 57604
[NH:1]1[CH2:5][CH2:4][CH:3]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH:2]12.[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31](ON3C(=O)CCC3=O)=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[N:1]1([C:31]([O:30][CH2:29][CH:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:28]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:32])[CH2:5][CH2:4][CH:3]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH:2]12

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 225622051,1-Dimethylethyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Produkt 1

HCID 711137921-(9H-fluoren-9-yl)methyl 5-tert-butyl hexahydropyrrolo[3,4-b]pyrrole-1,5-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (424 mg, 2 mmol), N-(9-fluorenylmethoxycarbonyloxy) succinimide (600 mg, 1.8 mmol) and DIPEA (310 mg, 2.4 mmol) in dioxane (20 mL) was stirred at room temperature overnight and then concentrated in vacuo. The residue was treated with EtOAc/H2O, separated, and the aqueous layer was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound. MS (m/z): 355 (M-boc+H)+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with EtOAc/H2O
  3. customseparated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bbb159d6afb54307a9d3653fb4fcc415
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434726B2

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