HCID 15292629, compound → HCID 131719743, compound

HRID 1080632Notes

Reaction equation

HRID 1080632 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][NH2:6].[OH:7][C@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@:14]3([OH:30])[CH2:15][CH2:16][C@@H:17]2[CH2:27][CH:28]=O)[CH2:9]1>[OH-].[Na+].O1CCOCC1>[NH2:2][CH2:3][CH2:4][O:5][N:6]=[CH:28][CH2:27][C@H:17]1[CH2:16][CH2:15][C@:14]2([OH:30])[C@H:13]3[C@H:22]([CH2:21][CH2:20][C@:18]12[CH3:19])[C@:23]1([CH3:26])[C@@H:10]([CH2:9][C@@H:8]([OH:7])[CH2:25][CH2:24]1)[CH2:11][CH2:12]3

Participants

5

Reactant 2

HCID 15292629HCID 15292629, compoundHCID 233652242-(Aminooxy)ethanamine hydrochloride

Product 1

HCID 131719743HCID 131719743, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 0.47 g of 2-aminoethoxyamine hydrochloride in 16 ml of 1N NaOH and 20 ml of dioxane a solution of 0.89 g of 3β,14β-dihydroxy-5β-androstane-17β-ylacetaldehyde (Prepn. 2) in 15 ml of dioxane was added at room temperature. After 20 hrs the solution was extracted with ethyl acetate; the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography (SiO2) using chloroform with increasing amounts of methanol (6 to 20%) as the eluant. The fractions containing the title compound were collected and evaporated to dryness. The residue was ground with di-iso-propyl ether to give 0.55 g of the title compound (I-bf), as a white foam.

Workup

  1. extractionAfter 20 hrs the solution was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by flash chromatography (SiO2)
  5. additionThe fractions containing the title compound
  6. customwere collected
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e3561d84c3754cf0943c1167493f7d35
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

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