Cyclohexanone → HCID 12804706, compound

HRID 223434Notes

Reaction equation

HRID 223434 reaction equation
C1O[C:4]([C@@H:6]2[C@:23]3([CH3:24])[C@H:9]([C@H:10]4[C@H:20]([C@H:21]([NH2:25])[CH2:22]3)[C@:18]3([CH3:19])[C@H:13]([CH2:14][C@H:15]([OH:29])[C@@H:16]([O:26][CH2:27][CH3:28])[CH2:17]3)[CH2:12][CH2:11]4)[CH2:8][CH2:7]2)([CH3:5])[O:3]C1.[C:31]1(=O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>C(O)C.Cl.O>[CH:31]1([NH:25][C@@H:21]2[CH2:22][C@@:23]3([CH3:24])[C@@H:9]([CH2:8][CH2:7][C@@H:6]3[C:4](=[O:3])[CH3:5])[C@H:10]3[C@H:20]2[C@:18]2([CH3:19])[C@@H:13]([CH2:12][CH2:11]3)[CH2:14][C@H:15]([OH:29])[C@@H:16]([O:26][CH2:27][CH3:28])[CH2:17]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

8

Reactant 4

HCID 7967CyclohexanoneHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 22821801HCID 22821801, compound

Product 1

HCID 12804706HCID 12804706, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 11α-amino-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one 20-ethylene acetal (2 g) in ethanol (20 ml) was stirred with cyclohexanone (1.5 ml) and sodium cyanoborohydride (2.015 g) for 6 h. 5% NaHCO3 solution (40 ml) was added and the mixture was extracted with ether (x2). The extract was washed with water (x2), dried and evaporated to leave a froth which was dissolved in 2M-HCl solution (50 ml) and ethanol (50 ml). Water (100 ml) was added and the mixture was washed with ether (x2). The wash was extracted with 2M-HCl solution and the combined acid fraction was brought to basic pH with 2M-NaOH solution. The mixture was extracted with ether (x2) and the extract was washed with water (x2), dried and evaporated to leave a froth which was purified by column chromatography eluted with CHCl3 :MeOH (9:1) to give the title compound (1.235 g), [α]D +39°. νmax 1695 cm-1.

Workup

  1. extractionthe mixture was extracted with ether (x2)
  2. washThe extract was washed with water (x2)
  3. customdried
  4. customevaporated
  5. customto leave a froth which
  6. washthe mixture was washed with ether (x2)
  7. extractionThe wash was extracted with 2M-HCl solution
  8. extractionThe mixture was extracted with ether (x2)
  9. washthe extract was washed with water (x2)
  10. customdried
  11. customevaporated
  12. customto leave a froth which
  13. customwas purified by column chromatography
  14. washeluted with CHCl3 :MeOH (9:1)

Sources & evidence

ORD record
ord-45054b6002454d509711c87a55c276dc
Source dataset
uspto-grants-1982_10
Patent number
US04353898

Reaction notes

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