Sodium → HCID 12804710, compound

HRID 223429Notes

Reaction equation

HRID 223429 reaction equation
C1CO[C:3]([C@@H:5]2[C@:22]3([CH3:23])[C@H:8]([C@H:9]4[C@H:19]([C:20](=[N:24]O)[CH2:21]3)[C@:17]3([CH3:18])[C@H:12]([CH2:13][CH:14]=[CH:15][CH2:16]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6]2)([CH3:4])[O:2]1.[Na]>C(O)CC>[NH2:24][C@@H:20]1[CH2:21][C@@:22]2([CH3:23])[C@@H:8]([CH2:7][CH2:6][C@@H:5]2[C:3](=[O:2])[CH3:4])[C@H:9]2[C@H:19]1[C@:17]1([CH3:18])[C@@H:12]([CH2:11][CH2:10]2)[CH2:13][CH:14]=[CH:15][CH2:16]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 131712856HCID 131712856, compound

Product 1

HCID 12804710HCID 12804710, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 20,20-ethylenedioxy-5α-pregn-2-en-11-one 11-oxime (9.36 g) in propan-1-ol (215 ml) was heated at reflux and sodium (8 g) was added over 2 hours. When all the sodium was consumed the propan-1-ol was removed by distillation. The residue was extracted with ether (x 3) and these extracts were extracted with 2 M-HCl solution (x 3). The extracts were washed with ether and brought to pH 9 with 0.88 NH3 solution. The mixture was extracted with ether (x 2) and the extracts were washed with water, dried and evaporated to leave a solid (8.77 g) which was crystallised from ethyl acetate/petrol to give the title compound (6.15 g) in two crops. A portion was recrystallised from ethyl acetate/petrol, m.p. 127°-129° C., [α]D +121°.

Workup

  1. temperatureat reflux
  2. customWhen all the sodium was consumed the propan-1-ol
  3. customwas removed by distillation
  4. extractionThe residue was extracted with ether (x 3)
  5. extractionthese extracts were extracted with 2 M-HCl solution (x 3)
  6. washThe extracts were washed with ether
  7. extractionThe mixture was extracted with ether (x 2)
  8. washthe extracts were washed with water
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-ac474315928d44f0aba67f7b0741eea6
Source dataset
uspto-grants-1982_10
Patent number
US04353898

Reaction notes

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