Sodium Hydroxide → HCID 67847883, compound

HRID 1492343

Reaction equation

HRID 1492343 reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH3:9][C@:10]12[CH2:27][CH2:26][C@H:25]3[C@@H:15]([CH2:16][CH2:17][C@@H:18]4[C@:23]3([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]4)[C@@H:14]1[CH2:13][CH2:12][C:11]2=O.C([BH3-])#N.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C.CO>[CH3:9][C@:10]12[CH2:27][CH2:26][C@H:25]3[C@@H:15]([CH2:16][CH2:17][C@@H:18]4[C@:23]3([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]4)[C@@H:14]1[CH2:13][CH2:12][C@@H:11]2[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][NH2:8]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 16402HexamethylenediamineHCID 1019275alpha-Androstan-17-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67847883HCID 67847883, compoundYield 124.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 100ml round-bottomed flask, equipped with a magnetic stir bar, condenser, and nitrogen inlet tube, was charged with 1,6-hexanediamine (0.904 g) and 15 ml of methanol. The solution was treated with glacial acetic acid until the pH was 6.7. To this mixture was added 15 ml of tetrahydrofuran, 5α-androstan-17-one (0.704 g) and sodium cyanoborohydride (0.228 g). The mixture was heated to reflux for 18 h. After cooling, the solution was made basic with aqueous 2M sodium hydroxide to a pH of 13-14. The solution was extracted with chloroform (3×) and the combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated to give 1.2 g of an oil.

Workup

  1. customA 100ml round-bottomed flask, equipped with a magnetic stir bar, condenser, and nitrogen inlet tube
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 18 h
  4. temperatureAfter cooling
  5. extractionThe solution was extracted with chloroform (3×)
  6. washthe combined organic layers were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-87273f30ab2f4cbb9a4e859f7e637c4b
Source dataset
uspto-grants-1994_12
Patent number
US05373095

Linked notes

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