Formaldehyde → HCID 10693544, compound

HRID 1449483Notes

Reaction equation

HRID 1449483 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][O:5][NH:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@:11]2([OH:28])[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C@@H:17]([CH2:18][C@@H:19]([OH:27])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3.C=O.[BH3-][C:33]#N.[Na+]>C(#N)C.Cl>[CH3:33][N:6]([CH2:7][C@H:8]1[CH2:13][CH2:12][C@:11]2([OH:28])[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C@@H:17]([CH2:18][C@@H:19]([OH:27])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)[O:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:29]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10621456HCID 10621456, compound

Product 1

HCID 10693544HCID 10693544, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 0.41 g of 17β-(2-dimethylaminoethoxyamino)methyl-5β-androstane-3β,14β-diol (I-am) and 1.0 ml of 37% aqueous formaldehyde in 10 ml of acetonitrile 0.20 g of NaBH3CN was added. The reaction was stirred for 28 hr and then diluted with 0.1N hydrochloric acid and extracted with ethyl acetate. The aqueous layer was basified to pH 9.5 with 2.5N NaOH and extracted with ethyl acetate; the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash-chromatography (SiO2) using chloroform/methanol/26% aqueous ammonium hydroxide 90/9/1 as the eluant; the fractions containing the title compound were collected and evaporated to dryness under reduced pressure. The residue was dissolved with ethyl acetate and the stoichiometric amount of oxalic acid was added to give 0.33 g of the title compound (I-ap), as a white solid, oxalate.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by flash-chromatography (SiO2)
  6. additionthe fractions containing the title compound
  7. customwere collected
  8. customevaporated to dryness under reduced pressure
  9. dissolutionThe residue was dissolved with ethyl acetate
  10. additionthe stoichiometric amount of oxalic acid was added

Sources & evidence

ORD record
ord-913cb3139ae14809ad5977d219474d5a
Source dataset
uspto-grants-1997_02
Patent number
US05599806

Reaction notes

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