9H-fluoren-9-ylmethyl-9-(phenylmethyl)-1-oxa-4,9-diazaspiro[5,5]undecane-4-carboxylate → 9H-fluoren-9-ylmethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

HRID 79233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79233
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C:22]4([CH2:28][CH2:27][N:26](CC5C=CC=CC=5)[CH2:25][CH2:24]4)[O:21][CH2:20][CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>C(O)C>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C:22]4([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[O:21][CH2:20][CH2:19]3)=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

3

Edukt 1

HCID 582996729H-fluoren-9-ylmethyl-9-(phenylmethyl)-1-oxa-4,9-diazaspiro[5,5]undecane-4-carboxylate

Produkt 1

HCID 683226439H-fluoren-9-ylmethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylateAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of compound 403 (1.43 g, 3.05 mmol) in ethanol (27 mL) was added palladium hydroxide, 20 wt % pd (dry basis) on carbon, wet (1.51 g, 2.15 mmol), followed by hydrochloric acid (0.10 mL). The sealed glass tube was then evacuated and purged with hydrogen three times. The sealed tube was then charged with hydrogen (50 psi), and allowed to stir at room temperature for three days. HPLC showed ˜85% conversion to the desired product. After filtering the mixture through a plug of celite, the filtrate was concentrated to a solid and purified by flash chromatography (0-20% methanol in DCM with 1% NH4OH) to give compound 404 (709 mg, 61%) as a white solid. LCMS-ESI (POS), M/Z, M+1: Found 379.1, Calculated 379.2.

Aufarbeitung

  1. dry with materialpalladium hydroxide, 20 wt % pd (dry basis) on carbon, wet (1.51 g, 2.15 mmol)
  2. customThe sealed glass tube was then evacuated
  3. custompurged with hydrogen three times
  4. additionThe sealed tube was then charged with hydrogen (50 psi)
  5. filtrationAfter filtering the mixture through a plug of celite
  6. concentrationthe filtrate was concentrated to a solid
  7. custompurified by flash chromatography (0-20% methanol in DCM with 1% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-338a1a00fa8b451eb96d6336ac6249a7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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