Acetic Acid → HCID 14800099, compound

HRID 2082253Notes

Reaction equation

HRID 2082253 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C@:11]12[CH2:28][CH2:27][C@H:26]3[C@@H:16]([CH2:17][CH2:18][C@@H:19]4[C@:24]3([CH3:25])[CH2:23][CH2:22][CH2:21][CH2:20]4)[C@@H:15]1[CH2:14][CH2:13][C@@H:12]2[NH2:29].C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:29][C@H:12]2[CH2:13][CH2:14][C@H:15]3[C@H:16]4[C@H:26]([CH2:27][CH2:28][C@:11]23[CH3:10])[C@:24]2([CH3:25])[C@H:19]([CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:18][CH2:17]4)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11254375HCID 11254375, compound

Product 1

HCID 14800099HCID 14800099, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorobenzaldehyde (0.464 g), 5α-androstan-17β-amine (4.40 g), glacial acetic acid (0.99 g), sodium cyanoborohydride (0.21 g) and tetrahydrofuran (5 ml) were added to methanol (11 ml). The resulting mixture was warmed to dissolve the solid in solution and allowed to stir overnight at room temperature. Excess solvent was removed under reduced pressure. Water was added and made basic (pH 9) with 50% aqueous NaOH. The mixture was extracted with ether and the organic layer became cloudy. Celite was used to filter the organic layer. The aqueous layer was washed with ether and the combined organic layers were dried (NaSO4), filtered and concentrated. The crude solid was mixed with 10 g of flash silica gel and dissolved in ethyl acetate. The solvent was removed and the silica was poured on top of the chromatographic column. The compound was eluted with 50% ethyl acetate-hexane. The title compound was obtained as a solid which was recrystallized from acetone (0.364 g) mp 101°-102° C. (PLA2, diabetes)

Workup

  1. temperatureThe resulting mixture was warmed
  2. dissolutionto dissolve the solid in solution
  3. customExcess solvent was removed under reduced pressure
  4. additionWater was added
  5. extractionThe mixture was extracted with ether
  6. filtrationto filter the organic layer
  7. washThe aqueous layer was washed with ether
  8. dry with materialthe combined organic layers were dried (NaSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. additionThe crude solid was mixed with 10 g of flash silica gel
  12. dissolutiondissolved in ethyl acetate
  13. customThe solvent was removed
  14. additionthe silica was poured on top of the chromatographic column
  15. washThe compound was eluted with 50% ethyl acetate-hexane

Sources & evidence

ORD record
ord-defbac0719994c56817a6ea2f5b85bd6
Source dataset
uspto-grants-1993_02
Patent number
US05187299

Reaction notes

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