Sodium cyanoborohydride → HCID 18947587, Verbindung

HRID 1769358Notizen

Reaktionsgleichung

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]([C:21](=O)[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:3]1[CH2:30][C:31]([CH3:37])([CH3:36])[C:32]([O:34][CH3:35])=[O:33].[BH3-]C#N.[Na+]>ClCCCl.[Zn+2].[I-].[I-]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:3]1[CH2:30][C:31]([CH3:37])([CH3:36])[C:32]([O:34][CH3:35])=[O:33]

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

To a solution of 500 mg of the benzoyl derivative from Step D of Example 24 in 10 mL of 1,2-dichloroethane were added 1.19 g of ZnI2 and 700 mg of NaBH3CN. The mixture was heated at 65° C. for 5 hours and cooled to R.T. The mixture was quenched with 1N aq. HCl and extracted with CH2Cl2. The extracts were washed with brine, dried over Na2SO4 and evaporated to dryness to give an oil which was chromatographed on flash silica gel using ethyl acetate:hexane (15:85) as eluant to isolate the title compound as a white foam.

Aufarbeitung

temperaturecooled to R.T
customThe mixture was quenched with 1N aq. HCl
extractionextracted with CH2Cl2
washThe extracts were washed with brine
dry with materialdried over Na2SO4
customevaporated to dryness
customto give an oil which
customwas chromatographed on flash silica gel

Quellen und Nachweise

ORD-Eintrag: ord-82456c03e1d1448fb8fbb51ba54e6bb4
Quelldatensatz: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05380850

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