2,3-Dihydroxybutanedioic Acid → N-t-Butyl-3-formylandrosta-3,5-diene-17beta-carboxamide

Temperature

0 °C

2 ml of a 1M solution of diisobutyl aluminum hydride in toluene were added at 0° C. to 10 ml of a dry solution of toluene containing 380 mg of N-t-butyl-3-cyanoandrosta-3,5-diene-17β-carboxamide (prepared as described in Preparation 2). The reaction mixture was then stirred at 0° C. for 30 minutes, after which 30 ml of an aqueous solution of 1.5 g of tartaric acid were added to the mixture. The reaction mixture was then stirred at room temperature for 2 hours, and then extracted with methylene chloride three times. The combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride, in that order. They were then dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 50 g of silica gel and using a gradient elution method, with mixtures of acetone and methylene chloride in ratios ranging from 1:99 to 4:96 by volume as the eluent, to give 325 mg of the title compound.

1. stirringThe reaction mixture was then stirred at room temperature for 2 hours
2. extractionextracted with methylene chloride three times
3. washThe combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride, in that order
4. dry with materialThey were then dried over anhydrous magnesium sulfate
5. concentrationconcentrated by evaporation under reduced pressure
6. washa gradient elution method

ORD record

ord-c76d59efb1ce43a2abfdd5246f8ed58a

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05536714