Studies with Deuterium Steroids 



31 



-J CH3-C00D ^f^T_J KOH ^jT^JLj 



1 



90% Yield 



ETHYL ORTHOFORMATE 



+ 



HCL 



L1AIH4 



d- TESTOSTERONE 

 0.79 gm. oloms D per mole 



Fig. 2. Synthesis of d-testosterone from androst-4-ene-3:17- 



dione. 







II 



Pt. 150° 



DgO- CD3COOD 



05N KOH, 



'E Hr. 

 Reflux 



5.73 D 



2N HCI^ 

 6 Hr. Reflux 



4.28 D 



3.20 D 



/m.p. 257-259° 

 ["^In ' "•" ISKChloroform) 

 6 2810* 2050 (Ethanol) 

 < Acefatej 3.25 



m.p. 126 5-127.5° 

 I [«.] = + l36(Chloroform) 

 Ve2680,2750 = '''*5 (Ethanol) 



Fig. 3. Preparation of d-oestrone by the platinum catalysed 



exchange reaction. 



