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

HRID 862301Notes

Reaction equation

HRID 862301 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([NH:15][C:16]([C@H:18]1[CH2:23][CH2:22][C@H:21]2[C@H:24]3[C@H:34]([CH2:35][CH2:36][C@:19]12[CH3:20])[C@:32]1([CH3:33])[C:27]([CH:28]=[C:29]([C:37]#N)[CH2:30][CH2:31]1)=[CH:26][CH2:25]3)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(O)(=O)C(C(C(O)=O)O)[OH:41]>C1(C)C=CC=CC=1>[C:11]([NH:15][C:16]([C@H:18]1[CH2:23][CH2:22][C@H:21]2[C@H:24]3[C@H:34]([CH2:35][CH2:36][C@:19]12[CH3:20])[C@:32]1([CH3:33])[C:27]([CH:28]=[C:29]([CH:37]=[O:41])[CH2:30][CH2:31]1)=[CH:26][CH2:25]3)=[O:17])([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 21225700DiisobutylaluminumhydrideHCID 676469513-Cyano-N-(1,1-dimethylethyl)androsta-3,5-diene-17-beta-carboxamide

Product 1

HCID 86749645N-t-Butyl-3-formylandrosta-3,5-diene-17beta-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

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 rhea 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.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 2 hours
  2. extractionrhea extracted 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

Sources & evidence

ORD record
ord-a199d2b518b44ed2a4c014df53c16b14
Source dataset
uspto-grants-1998_02
Patent number
US05717088

Reaction notes

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