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Ammonia → tert-Butyl 4-(((benzyloxy)carbonyl)amino)-4-carbamoylpiperidine-1-carboxylate

HRID 1013079
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1013079
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:25]([OH:27])=O)[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:29]1CCOCC1.N>COCCOC>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:25](=[O:27])[NH2:29])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 27566404-(((Benzyloxy)carbonyl)amino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

Produkt 1

HCID 10714606tert-Butyl 4-(((benzyloxy)carbonyl)amino)-4-carbamoylpiperidine-1-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8071
1,2-Dimethoxyethane
Lösungsmittel

Versuchsvorschrift

A solution 4-(benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1A, 2.0 g, 1.0 equivalent) in DME (0.5 M) was treated with NMM (1.0 equivalent) and IBCF (1.0 equivalent) at −15° C. After 10 min, aqueous ammonia (1.5 equivalents) was added. The reaction mixture was stirred at room temperature for 1.5 hr. The reaction was complete as determined by LCMS analysis and then partitioned between ethyl acetate and water. The organics were subsequently washed with brine, then dried over Na2SO4, filter, and the volatiles removed under reduced pressure. The residue was purified by crystallization from diethyl ether to afford the tert-butyl 4-(benzyloxycarbonylamino)-4-carbamoylpiperidine-1-carboxylate (1B, 70%).

Aufarbeitung

  1. custompartitioned between ethyl acetate and water
  2. washThe organics were subsequently washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfilter
  5. customthe volatiles removed under reduced pressure
  6. customThe residue was purified by crystallization from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6641a2ce37c14ff9ac554266145e6866
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07981904B2

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