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

HRID 962698Notes

Reaction equation

HRID 962698 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 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.

Workup

  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

Sources & evidence

ORD record
ord-80f184ecd11049a8a528b719e688d85d
Source dataset
uspto-grants-1998_06
Patent number
US05760025

Reaction notes

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