Diisobutylaluminumhydride → HCID 73096807、化合物

温度

-78 °C

1-methyl ester and 3-tert-butoxycarbonylamino-2,2-dimethyl-succinic acid dimethyl ester (0.47 g, 1.53 mmol) was dissolved in dichloromethane (3 mL) and cooled to −78° C. Diisobutylaluminum hydride (3.4 mL of a 1M dichloromethane solution, 3.4 mmol) was slowly added. The reaction mixture was warmed to room temperature with stirring over 16 h. Additional diisobutylaluminum hydride (a total of 6.8 mL of a 1M solution, 6.8 mmol) was added portionwise over the next 24 h until thin layer chromatography indicated the starting material was consumed. Aqueous ammonium chloride solution and ethyl acetate were added to the reaction, the layers were separated and the aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with sodium chloride solution and dried over sodium sulfate. After evaporation, the residue was purified by silica gel chromatography (ethyl acetate/hexanes) to give 104 mg (29%) of (3-hydroxy-1-hydroxymethyl-2,2-dimethyl-propyl)-carbamic acid tert-butyl ester.

1. temperatureThe reaction mixture was warmed to room temperature
2. customwas consumed
3. additionAqueous ammonium chloride solution and ethyl acetate were added to the reaction
4. customthe layers were separated
5. extractionthe aqueous layer was extracted once more with ethyl acetate
6. washThe combined organic layers were washed with sodium chloride solution
7. dry with materialdried over sodium sulfate
8. customAfter evaporation
9. customthe residue was purified by silica gel chromatography (ethyl acetate/hexanes)

ORDレコード

ord-ac7bb1d0aa2341bf8fbba857c77aa4f2

出典データセット

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08329699B2