Ammonium formate → (9,9-Dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone

HRID 713139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 713139
C([N:8]1[C:31]([CH3:33])([CH3:32])[CH2:30][O:29][C:10]2([CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([CH3:28])[CH:19]=3)=[O:17])[CH2:12][CH2:11]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:33][C:31]1([CH3:32])[CH2:30][O:29][C:10]2([CH2:11][CH2:12][N:13]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([CH3:28])[CH:19]=3)=[O:17])[CH2:14][CH2:15]2)[CH2:9][NH:8]1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 70872805(8-Benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone

Produkt 1

HCID 66548351(9,9-Dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanoneAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of (8-benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone (51 mg, 0.11 mmol) in ethanol (2 mL) was added Pd(OH)2 (16 mg, 0.11 mmol) followed by ammonium formate (29 mg, 0.45 mmol). The reaction mixture was stirred at 40° C. for 18 h, then filtered and concentrated in vacuo to afford (9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone (40 mg, 98%). ESI-MS m/z calc. 360.5. found 361.3 (M+1)+; Retention time: 1.29 minutes (3 min run).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-85ac8df7f3ef4dd08495d62f77ad31a2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181273B2

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