Triphenylphosphine → Carbamic acid, [2-oxo-1-(phenylmethoxy)-1-azaspiro[3.3]hept-3-yl]-, 1,1-dimethylethyl ester

HRID 980579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 980579
[CH2:1]([O:8][NH:9][C:10](=[O:25])[CH:11]([C:20]1(O)[CH2:23][CH2:22][CH2:21]1)[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>O1CCCC1>[CH2:1]([O:8][N:9]1[C:20]2([CH2:23][CH2:22][CH2:21]2)[CH:11]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylateHCID 13754455HCID 13754455, VerbindungHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 13754458Carbamic acid, [2-oxo-1-(phenylmethoxy)-1-azaspiro[3.3]hept-3-yl]-, 1,1-dimethylethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-(Benzyloxy)-N2 -(t-butoxycarbonyl)-α-(1-hydroxycyclobutyl)glycinamide (3.50 g, 10 mmole) in 200 ml of dry tetrahydrofuran at 0° C. under argon was treated with 2.4 ml (15 mmole) of diethylazodicarboxylate, then with a solution of triphenylphosphine (5.2 g, 20 mmole) in 50 ml of tetrahydrofuran over 10 minutes, and the mixture stirred at 0° C. for one hour. The yellow color persisted so an additional 0.52 g (2 mmole) of triphenylphosphine was added. After 15 minutes, evaporation in vacuo gave an oil. Trituration with 100 ml of hexane:ethyl acetate (2:1) gave a white solid which was filtered. Chromatography of the filtrate on 800 ml of LPS-1 gave product fractions [Rf=0.8 in hexane:ethyl acetate (1:1)] contaminated with a close-running impurity which was removed by trituration with isopropyl ether, giving the product as a white solid, 1.07 g, melting point 156°-157° C.

Aufarbeitung

  1. additionwas added
  2. waitAfter 15 minutes
  3. customevaporation in vacuo
  4. customgave an oil
  5. filtrationwas filtered
  6. customwas removed by trituration with isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b19c8b6b6f694aad91402fb024839e6a
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04638060

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