HCID 86736928, compound → HCID 12796475, compound

HRID 2049486Notes

Reaction equation

HRID 2049486 reaction equation
[OH:1][C@@H:2]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:17]2[C:16](=[N:22]O)[CH2:15][C@@:14]2([CH3:24])[C@H:8]3[CH2:9][CH2:10]/[C:11]/2=[CH:12]/[CH3:13])[CH2:3]1>C(O)CC>[NH2:22][C@@H:16]1[CH2:15][C@@:14]2([CH3:24])[C@@H:8]([CH2:9][CH2:10]/[C:11]/2=[CH:12]/[CH3:13])[C@H:7]2[C@H:17]1[C@:18]1([CH3:21])[C@@H:4]([CH2:5][CH2:6]2)[CH2:3][C@H:2]([OH:1])[CH2:20][CH2:19]1

Participants

3

Reactant 1

HCID 86736928HCID 86736928, compound

Product 1

HCID 12796475HCID 12796475, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of (Z)-3α-hydroxy-5α-pregn-17(20)-en-11-one oxime (9.638 g) in propan-1-ol (200 ml) was refluxed under N2 whilst Na (9.6 g) was added portionwise. When all of the Na had reacted, about 90 ml propan-1-ol was distilled and then the residue was poured into water, ice was added and the crystalline solid (9.19 g) was collected by filtration. A portion (6.17 g) was crystallised from ethanol-water to afford title compound (3.6 g), m.p. 118°-125°, [α]D +5.4°.

Workup

  1. additionwas added portionwise
  2. distillationabout 90 ml propan-1-ol was distilled
  3. additionthe residue was poured into water, ice
  4. additionwas added
  5. filtrationthe crystalline solid (9.19 g) was collected by filtration
  6. customA portion (6.17 g) was crystallised from ethanol-water

Sources & evidence

ORD record
ord-4ebc04300dec457fa1875fb7f696a22f
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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