Acetic Acid → Benzyl 4-{[1-(methoxycarbonyl)but-3-en-1-yl]amino}piperidine-1-carboxylate

HRID 20083

Reaktionsgleichung

Reaktionsgleichung von HRID 20083
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][CH:16]([CH2:21][CH:22]=[CH2:23])[C:17]([O:19][CH3:20])=[O:18].C(O)(=O)C.O=[C:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:36])[CH2:31][CH2:30]1>ClC(Cl)C>[CH3:20][O:19][C:17]([CH:16]([NH:15][CH:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:36])[CH2:31][CH2:30]1)[CH2:21][CH:22]=[CH2:23])=[O:18]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 10877146Methyl 2-aminopent-4-enoate

Produkt 1

HCID 22293179Benzyl 4-{[1-(methoxycarbonyl)but-3-en-1-yl]amino}piperidine-1-carboxylateAusbeute 103,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (11.2 g, 52.6 mmol) was added to a solution of methyl 2-aminopent-4-enoate (3.4 g, 26.3 mmol), acetic acid (2.37 g, 39.5 mmol) and benzyl 4-oxopiperidine-1-carboxylate (9.21 g, 39.5 mmol) in dichloroethane (60 mL) at room temperature. After 3 h, the reaction was quenched with saturated aqueous sodium bicarbonate, extracted with methylene chloride (3×), dried over sodium sulfate, filtered and evaporated to give the crude product. This was purified by chromatography (silica gel, 0 to 8% methanol in methylene chloride gradient elution), which gave the title compound (9.42 g). MS 347.2 (M+1).

Aufarbeitung

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with methylene chloride (3×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give the crude product
  7. customThis was purified by chromatography (silica gel, 0 to 8% methanol in methylene chloride gradient elution), which

Quellen und Nachweise

ORD-Eintrag
ord-33c0580e28f64c06ae5e7467e5c2b669
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745427B2

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