Acetic Acid → HCID 20578939, Verbindung

HRID 1594243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594243
[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][C:4]([N:6]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)[C@@H:7]1[CH2:11][NH:10][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]1)=[O:5].[CH:27]1[C:32]([CH:33]=O)=[CH:31][C:30]2[O:35][CH2:36][O:37][C:29]=2[CH:28]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>O1CCCC1>[O:37]1[C:29]2[CH:28]=[CH:27][C:32]([CH2:33][N:10]3[CH2:11][C@@H:7]([N:6]([C:4](=[O:5])[CH2:3][C:2]([CH3:26])([CH3:25])[CH3:1])[CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=4)[CH2:8][C@H:9]3[C:12]([O:14][CH3:15])=[O:13])=[CH:31][C:30]=2[O:35][CH2:36]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8438PiperonalHCID 5003444Sodium cyanoborohydrideHCID 20578916HCID 20578916, Verbindung

Produkt 1

HCID 20578939HCID 20578939, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl (2S,4S)-4-[(3,3-dimethylbutanoyl)(3-methoxybenzyl)amino]-tetrahydro-1H-2-pyrrolecarboxylate (19b) (138 mg, 0.38 mmol), piperonal (58 mg, 0.39 mmol) and glacial acetic acid (225 μL, 3.93 mmol) in tetrahydrofuran (2.8 mL) was stirred for 30 min at room temperature. 95% Sodium cyanoborohydride (125 mg, 1.88 mmol) was added in small portions and stirring was continued for 45 min at the same temperature. After dilution with ethyl acetate (5 mL), the reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution (2×5 mL) and brine (5 mL), dried (MgSO4) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography eluting with 100% dichloromethane and dichloromethane-ethylacetate (4:1, v/v) to give the title pyrrole (20):

Aufarbeitung

  1. washAfter dilution with ethyl acetate (5 mL), the reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution (2×5 mL) and brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with 100% dichloromethane and dichloromethane-ethylacetate (4:1

Quellen und Nachweise

ORD-Eintrag
ord-1b45e5d906b7416aa4d318bd142d98b6
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07300929B2

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