Water → HCID 69790431, compound

HRID 895852Notes

Reaction equation

HRID 895852 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][C:5]1([CH3:39])[C@@H:35](O)[CH2:34][CH2:33][C@@:32]2([CH3:37])[CH:6]1[CH2:7][CH2:8][C:9]1[C:10]3[C@:28]([CH3:38])([CH2:29][CH2:30][C:31]=12)[C@@H:13]([C@H:14]([CH3:27])[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:12][CH:11]=3.[OH2:40]>CS(C)=O>[OH:40][C@H:35]1[CH2:34][CH2:33][C@@:32]2([CH3:37])[CH:6]([CH2:7][CH2:8][C:9]3[C:10]4[C@:28]([CH3:38])([CH2:29][CH2:30][C:31]=32)[C@@H:13]([C@@H:14]([CH3:27])[CH2:15][C:1]#[N:2])[CH2:12][CH:11]=4)[C:5]1([CH3:39])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 86586580HCID 86586580, compound

Product 1

HCID 69790431HCID 69790431, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

1.7 g potassium cyanide were added to a solution of 4.7 g (20S)-4,4,20-trimethyl-21-tosyloxy-pregna-8,14-dien-3β-ol in 90 ml DMSO at room temperature. The mixture was stirred for 2 h at 90° C., poured into water, extracted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2.8 g (20S)-3β-hydroxy-4,4,20-trimethyl-pregna-8,14-dien-21-carbonitril as a white solid which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a89524161405445aa993a3677b85ccb6
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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