Acetic Acid → HCID 14800097, compound

HRID 1614477Notes

Reaction equation

HRID 1614477 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][CH2:12][CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[NH2:20].C(O)(=O)C.C([BH3-])#N.[Na+].[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CO.O1CCCC1>[CH2:29]([NH:20][C@H:3]1[CH2:4][CH2:5][C@H:6]2[C@H:7]3[C@H:17]([CH2:18][CH2:19][C@:2]12[CH3:1])[C@:15]1([CH3:16])[C@H:10]([CH2:11][CH2:12][CH2:13][CH2:14]1)[CH2:9][CH2:8]3)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11254375HCID 11254375, compound

Product 1

HCID 14800097HCID 14800097, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5α-Androstan-17β-amine (10.946 g), glacial acetic acid (2.39 g), sodium cyanoborohydride (0.50 g), benzaldehyde (0.84 g) and tetrahydrofuran (50 ml) were added to methanol (25 ml). The resulting mixture was stirred at room temperature for 48 hours. Excess solvent was removed under reduced pressure. Water was added and made basic (pH 9) with 50% aqueous NMaOH. The mixture was extracted with ether (3×). The combined extracts were dried, filtered and concentrated to a solid. The solid was mixed with 20 g of flash silica gel and dissolved in ethyl acetate. The solvent was removed at reduced pressure and the silica gel was poured on top of the chromatographic column. The compound was eluted with 5% triethylamine-ethylacetate. 6 fractions (200 ml) were collected. An oil was obtained and was dissolved in hot methanol. The solution was cooled giving colorless crystals, mp 85.5°-87.5° C. (PLA2, diabetes)

Workup

  1. customExcess solvent was removed under reduced pressure
  2. additionWater was added
  3. extractionThe mixture was extracted with ether (3×)
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated to a solid
  7. additionThe solid was mixed with 20 g of flash silica gel
  8. dissolutiondissolved in ethyl acetate
  9. customThe solvent was removed at reduced pressure
  10. additionthe silica gel was poured on top of the chromatographic column
  11. washThe compound was eluted with 5% triethylamine-ethylacetate
  12. custom6 fractions (200 ml) were collected
  13. customAn oil was obtained
  14. temperatureThe solution was cooled
  15. customgiving colorless crystals, mp 85.5°-87.5° C. (PLA2, diabetes)

Sources & evidence

ORD record
ord-b86794d703784c55a964eee4b9dc4321
Source dataset
uspto-grants-1993_03
Patent number
US05196542

Reaction notes

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