HCID 70583577, compound → HCID 70583955, compound

HRID 2049480Notes

Reaction equation

HRID 2049480 reaction equation
C[Li].C1(C)C=CC(S(NN=[C:14]2[CH2:19][CH2:18][C@H:17]3[C@H:20]4[C@H:30]([C@H:31]([N:33]([CH3:35])[CH3:34])[CH2:32][C@:15]23[CH3:16])[C@:28]2([CH3:29])[C@H:23]([CH2:24][C@H:25]([OH:39])[C@@H:26]([O:36][CH2:37][CH3:38])[CH2:27]2)[CH2:22][CH2:21]4)(=O)=O)=CC=1>CCOCC.O1CCCC1>[CH3:34][N:33]([C@@H:31]1[CH2:32][C@@:15]2([CH3:16])[C@@H:17]([CH2:18][CH:19]=[CH:14]2)[C@H:20]2[C@H:30]1[C@:28]1([CH3:29])[C@@H:23]([CH2:22][CH2:21]2)[CH2:24][C@H:25]([OH:39])[C@@H:26]([O:36][CH2:37][CH3:38])[CH2:27]1)[CH3:35]

Participants

5

Reactant 2

HCID 70583577HCID 70583577, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 70583955HCID 70583955, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1.5 M solution of methyl lithium in ether (20 ml) was added to a cooled solution of 11α-N,N-dimethylamino-2β-ethoxy-3α-hydroxy-5α-androstan-17-one 17-p-toluenesulphonylhydrazone (1.2 g) in dry tetrahydrofuran (100 ml). The mixture was kept at room temperature for three days and then most of the solvent was evaporated in vacuo. The residue was acidified with 2 N-hydrochloric acid, washed with ether, and the aqueous layer was then basified with 2 N-sodium hydroxide and extracted into ether. The washed and dried (Na2SO4) extract was evaporated in vacuo and the residue was purified by chromatography over silica (ethyl acetate-petroleum ether 1:1) and crystallization from aqueous methanol to give the title compound m.p. 51°-54°, [α]D -23.8°.

Workup

  1. custommost of the solvent was evaporated in vacuo
  2. washwashed with ether
  3. extractionextracted into ether
  4. washThe washed
  5. dry with materialdried (Na2SO4)
  6. extractionextract
  7. customwas evaporated in vacuo
  8. customthe residue was purified by chromatography over silica (ethyl acetate-petroleum ether 1:1) and crystallization from aqueous methanol

Sources & evidence

ORD record
ord-a31a99579d3d444d9877d2ba07e99675
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

Loading…