Acetic Acid → 3beta-[N-(2-AMINOETHYL)-AMINO]-17beta-HYDROXY-5alpha-ANDROSTANE

HRID 375673

Reaction equation

HRID 375673 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=O)[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[CH2:22]([NH2:25])[CH2:23][NH2:24].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[NH2:24][CH2:23][CH2:22][NH:25][C@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C@@H:2]2[OH:1])[CH2:12]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 10635DihydrotestosteroneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 153088353beta-[N-(2-AMINOETHYL)-AMINO]-17beta-HYDROXY-5alpha-ANDROSTANE

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17β-Hydroxy-5α-androstan-3-one (403 mg, 1.39 mmol)(Aldrich Chemical Company) was added to a stirred solution of 0.745 mL 1,2-ethylenediamine (11.1 mmol) and 1.44 mL acetic acid (25.2 mmol) in 16.0 mL dry methanol (MeOH), followed by 104 mg (1.65 mmol, 1.19 equiv.) of sodium cyanoborohydride. After stirring at room temperature for 15 h, the reaction concentrated under reduced pressure. The residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide, shaken, and separated. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The product was used without further purification.

Workup

  1. concentrationthe reaction concentrated under reduced pressure
  2. customThe residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide
  3. stirringshaken
  4. customseparated
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was used without further purification

Sources & evidence

ORD record
ord-1c2136c9e3014b3da2cb9b7402937b62
Source dataset
uspto-grants-1996_01
Patent number
US05486603

Linked notes

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