Sodium Bicarbonate → HCID 12095978, compound

HRID 2219062Notes

Reaction equation

HRID 2219062 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@:16]3([C:20]#N)[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[CH2:11][C@H:10]([OH:22])[CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(=O)(O)[O-:34].[Na+]>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@:16]3([CH:20]=[O:34])[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[CH2:11][C@H:10]([OH:22])[CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12095977HCID 12095977, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 12095978HCID 12095978, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

A suspension that consists of 100 mg (0.34 mmol) of 3,16α-dihydroxyestra-1,3,5(10)-triene-9 carbonitrile in 40 ml of toluene is cooled to about −20° C. while being stirred. After 0.9 ml (1.35 mmol) of diisobutylaluminium hydride is added, the reaction is mixed after about 10 minutes with sodium bicarbonate solution, filtered over Celite, and the filtering adjuvant is extracted again with ethyl acetate. The combined organic phases are washed with water. By concentration by evaporation of the solution in a vacuum, 84.6 mg of a light yellow foam is obtained. The product that is contained in the mixture corresponds to a yield of about 52% of theory and is used without further chromatographic working-up in the next stage.

Workup

  1. filtrationfiltered over Celite
  2. extractionthe filtering adjuvant is extracted again with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. concentrationBy concentration
  5. customby evaporation of the solution in a vacuum

Sources & evidence

ORD record
ord-f0375e0a1d774467a6e94fa3c81bf816
Source dataset
uspto-grants-2008_08
Patent number
US07414043B2

Reaction notes

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