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tert-Butyl 4-oxopiperidine-1-carboxylate → 1,1-Dimethylethyl 4-{[4-(benzyloxy)-2-(methoxycarbonyl)phenyl]amino}piperidine-1-carboxylate

HRID 403547
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 403547
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O=[C:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.CCOC(C)=O>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 11288356Methyl 2-amino-5-(benzyloxy)benzoate2×

Produkt 1

HCID 595872031,1-Dimethylethyl 4-{[4-(benzyloxy)-2-(methoxycarbonyl)phenyl]amino}piperidine-1-carboxylateAusbeute 297,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2 g of methyl 2-amino-5-(benzyloxy)benzoate, 3.1 g of 1,1-dimethylethyl 4-oxopiperidine-1-carboxylate and 3.29 g of NaBH(OAc)3 in 10 ml of AcOH is irradiated under a microwave field (Biotage Initiator Sixty) at 110° C. for 20 min. The same reaction is repeated with two other lots of 2 g of methyl 2-amino-5-(benzyloxy)benzoate. The three reaction media are combined. The combined product is taken up in AcOEt. The organic phase is washed with water, with a saturated NH4Cl solution and with a saturated NaHCO3 solution, dried over Na2SO4 and filtered, and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with an AcOEt/heptane mixture, (5/95, v/v) as far as (30170, v/v), to give 10.2 g of the expected product.

Aufarbeitung

  1. customThe same reaction
  2. customThe three reaction media
  3. washThe organic phase is washed with water, with a saturated NH4Cl solution and with a saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-6a7f44ae9e81468dab6aacf94d207c02
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08748441B2

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