Diphenylsilane → 1,1-Dimethylethyl 1-(4-chlorophenyl)-2-cyclopropyl-2,7-diazaspiro[3.5]nonane-7-carboxylate

HRID 1869227

Reaktionsgleichung

Reaktionsgleichung von HRID 1869227
O=[C:2]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH:4]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:3]1[CH:25]1[CH2:27][CH2:26]1.C1([SiH2]C2C=CC=CC=2)C=CC=CC=1>C1COCC1.[C-]#[O+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Rh]>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH:4]2[C:5]3([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:7][CH2:6]3)[CH2:2][N:3]2[CH:25]2[CH2:27][CH2:26]2)=[CH:19][CH:20]=1

Komponenten

5

Edukt 2

HCID 69888DiphenylsilaneHCID 24954507HCID 24954507, Verbindung

Produkt 1

HCID 579860421,1-Dimethylethyl 1-(4-chlorophenyl)-2-cyclopropyl-2,7-diazaspiro[3.5]nonane-7-carboxylateAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10941995Carbonylhydridotris(triphenylphosphine)rhodium(I)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, treat 1,1-dimethylethyl 1-oxo-3-(4-chlorophenyl)-2-cyclopropyl-2,7-diazaspiro[3.5]nonane-7-carboxylate (9) (0.76 g) in anhydrous THF (2 mL) with RhH(CO)(PPH3)3 (18 mg) and then, diphenylsilane (9.1 mL). The resulting mixture was shaken at room temperature for 2 h. Place the reaction mixture on silica gel plates (12, 1000 u) and elute with hexane/EtOAc 85/15 to give a colorless residue (0.700 g). Place this material on silica gel plates (12, 1000 u) and elute with hexane/EtOAc 85/15 to give the title compound (10) as a colorless foam (0.58 g)

Aufarbeitung

  1. washelute with hexane/EtOAc 85/15

Quellen und Nachweise

ORD-Eintrag
ord-50fd09f961b948ee9b00b4150ec544bb
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638526B2

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