3beta,14beta-Dihydroxy-5beta-androstane-17beta-carboxaldehyde → HCID 178421251, compound

HRID 1735737Notes

Reaction equation

HRID 1735737 reaction equation
I.[C:2]1([NH:8][C:9](=[NH:12])[NH:10][NH2:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:13][C@H:14]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:28]2[CH2:27][CH2:26][C@@:24]2([CH3:25])[C@:20]3([OH:35])[CH2:21][CH2:22][C@@H:23]2[CH:33]=O)[CH2:15]1>O.O1CCOCC1>[C:2]1([NH:8][C:9](=[NH:12])[NH:10]/[N:11]=[CH:33]/[C@H:23]2[CH2:22][CH2:21][C@:20]3([OH:35])[C@H:19]4[C@H:28]([CH2:27][CH2:26][C@:24]23[CH3:25])[C@:29]2([CH3:32])[C@@H:16]([CH2:15][C@@H:14]([OH:13])[CH2:31][CH2:30]2)[CH2:17][CH2:18]4)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 109033043beta,14beta-Dihydroxy-5beta-androstane-17beta-carboxaldehydeHCID 178506602HCID 178506602, compound

Product 1

HCID 178421251HCID 178421251, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 0.83 g of 3-phenyl-1-aminoguanidine hydroiodide (prepared following the procedure described in Houben-Weil, Metoden der Organischen Chemie, Band VIII, page 183) in 10 ml of water and 5 ml of dioxane a solution of 0.64 g of 3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde (Boutagy J. and Thomas R., Aust. J. Chem., 1971, 24, 2723) in 5 ml of dioxane was added dropwise at room temperature. After 2 hrs, the solution was evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 89/10/1 as eluant; the fractions containing the title compound were collected and evaporated to dryness. The residue was ground with ethanol to give 0.20 g of the title compound (I-ah) as a white solid.

Workup

  1. customthe solution was evaporated to dryness under reduced pressure
  2. customThe crude product was purified by flash-chromatography (SiO2)
  3. additionthe fractions containing the title compound
  4. customwere collected
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8ca86461f15d4f76a8f6959cee5f6d15
Source dataset
uspto-grants-1996_07
Patent number
US05538960

Reaction notes

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