Potassium Cyanide → HCID 15481973, compound

HRID 1006405Notes

Reaction equation

HRID 1006405 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@:11]([CH2:36][CH2:37]I)([CH2:12][CH2:13][C@@H:14]3[C:23]2=[CH:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C-:39]#[N:40].[K+]>CN(C=O)C>[Si:1]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@:11]([CH2:36][CH2:37][C:39]#[N:40])([CH2:12][CH2:13][C@@H:14]3[C:23]2=[CH:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 15481965HCID 15481965, compound

Product 1

HCID 15481973HCID 15481973, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 2.23 g (3.31 mmol) of 3β,17β-bis-(tert-butyldimethylsilyloxy)-5-(2-iodoethyl)-5β-androst-9(11)-ene (Example 4e) and 948 mg (15.11 mmol) of KCN in 48 ml of DMF is stirred for 36 hours at 60° C. under argon. After cooling, it is poured into ice-cold 1N NaOH solution and extracted with dichloromethane. After chromatography of the crude product on silica gel with hexane/ethyl acetate, 1.56 g (75.5% of theory) of the nitrile with a melting point of 194-195° C. (hexane), [α]D +15.0° (CHCl3, c=0.5), is obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-83042b071d9147e3902630dab2b98073
Source dataset
uspto-grants-2004_09
Patent number
US06790843B1

Reaction notes

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