ChemicalBook CAS DataBase List Sodium cyanoborohydride

Sodium cyanoborohydride synthesis

4synthesis methods

Product Name:Sodium cyanoborohydride
CAS Number:25895-60-7
Molecular formula:CH3BNNa
Molecular Weight:62.84

Synthesis of Sodium cyanoborohydride(NaBH3CN): NaBH3CN was made by stirring equimolar BH3·THF (~1 M) with NaCN in THF in excellent yield.To a rapidly stirred slurry of sodium borohydride (80.2g, 2.09 mol) in THF (1000mL) in a 2-L flask is added a solution of hydrogen cyanide in THF (294g containing 58.8g of hydrogen cyanide) at 25°C. Evolution of hydrogen occurs slowly during the addition. Following the addition, the reaction mixture is stirred for 1 h at 25°C and then heated at reflux until hydrogen evolution has ceased. Filtration followed by vacuum removal of THF gives white solid sodium cyanoborohydride; yield 120g (91%).

Cyclopropanecarboxamide, 1-(3,4-dichlorophenyl)-N-[(4-fluorophenyl)methyl]-2-formyl-N-methyl-, (1S,2R)-

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52509-14-5 Synthesis

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide

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Yield:25895-60-7 91%

Reaction Conditions:

with potassium hexamethylsilazane in tetrahydrofuran at 20; for 2 h;

Steps:

17

Example 17 (LS, 2S)-L- (3, 4-DICHLORO-PHENYL)-2- ( (Z/E)-2- [1, 3] dioxolan-2-yl-vinyl)- cyclopropanecarboxylic acid (4-FLUORO-BENZYL)-METHYL-AMIDE (1, 3-Dioxolan-2-ylmethyl) triphenylphosphonium bromide (3.39 g, 7.89 mmol) is suspended in dry THF (50 ml) under Argon and KHMDS (1.57 g, 7.89 mmol) is added portionwise at 0°C. The mixture is stirred at 0°C for 30 minutes, then allowed to warm to ambient temperature. (lS, 2R)-1- (3, 4-DICHLORO-PHENYL)-2-FORMYL-CYCLOPROPANECARBOXYLIC acid (4- fluoro-benzyl) -methyl-amide (1.0 g, 2.63 mmol) dissolved in dry THF (10 ml) is added dropwise and the mixture is stirred at ambient temperature for 2 hours. The reaction mixture is then poured onto ice cold water (30 ml) and the layers are separated. The aqueous phase is extracted with ethyl acetate (3 X 30 ml) and the combined organic fractions are washed with brine (sat. ), dried (MGS04), filtered and concentrated in vacuo. The crude product is purified by silica gel chromatography, eluting with a gradient of ethyl acetate: heptane (20: 80)- (50 : 50). The product is isolated as a Z/E isomer mixture. Yield 1.07 g (91%). LC/MS (ONLY) 450.1 (M+H+).

References:

WO2005/16884,2005,A1 Location in patent:Page/Page column 66-67