Formaldehyde → HCID 18641819, compound

HRID 1089423Notes

Reaction equation

HRID 1089423 reaction equation
[CH2:1]=O.[CH:3]1([NH:6][C@H:7]2[CH2:12][CH2:11][C@H:10]3[C@H:13]4[C@H:23]([CH2:24][CH2:25][C@:8]23[CH3:9])[C@:21]2([CH3:22])[C:16]([C:17]([F:28])([F:27])[C@@H:18]([OH:26])[CH2:19][CH2:20]2)=[CH:15][CH2:14]4)[CH2:5][CH2:4]1.[OH-].[Na+]>C(O)=O>[F:28][C:17]1([F:27])[C@@H:18]([OH:26])[CH2:19][CH2:20][C@@:21]2([CH3:22])[C:16]1=[CH:15][CH2:14][C@@H:13]1[C@@H:23]2[CH2:24][CH2:25][C@@:8]2([CH3:9])[C@H:10]1[CH2:11][CH2:12][C@@H:7]2[N:6]([CH:3]1[CH2:5][CH2:4]1)[CH3:1]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 67742355HCID 67742355, compound

Product 1

HCID 18641819HCID 18641819, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a mixture of 10 ml of formic acid and 5 ml of formaldehyde is added 1.4 g of 17β-(cyclopropylamino)-4,4-difluoroandrost-5-en-3β-ol. The mixture is heated at reflux for 5 hours, the volume is then reduced to 7.5 ml in vacuo, and 10 ml of 50% (w/w) aqueous sodium hydroxide is added. The aqueous layer is separated and extracted with ethyl acetate and the combined organic solutions are dried over magnesium sulfate. The solvent is then removed in vacuo and the residual product is purified by flash chromatography to give 4,4-difluoro-17β-[N-methyl(cyclopropylamino)]androst-5-en-3β-ol.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 5 hours
  3. additionis added
  4. customThe aqueous layer is separated
  5. extractionextracted with ethyl acetate
  6. dry with materialthe combined organic solutions are dried over magnesium sulfate
  7. customThe solvent is then removed in vacuo
  8. customthe residual product is purified by flash chromatography

Sources & evidence

ORD record
ord-5532f2d518f642688abb0bb5c6da7b28
Source dataset
uspto-grants-1990_10
Patent number
US04966898

Reaction notes

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