Formaldehyde → HCID 15009207, compound

HRID 1461552Notes

Reaction equation

HRID 1461552 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]([CH2:17][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>[CH3:1][N:6]([CH:3]1[CH2:4][CH2:5]1)[C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C:16]([CH2:17][C@@H:18]([OH:26])[CH2:19][CH2:20]1)=[CH:15][CH2:14]3

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 9862308HCID 9862308, compound

Product 1

HCID 15009207HCID 15009207, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-06c51d63c09b4ffba8cd43acca907d93
Source dataset
uspto-grants-1991_12
Patent number
US05075464

Reaction notes

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