HCID 12961991, compound → HCID 12961993, compound

HRID 1065707Notes

Reaction equation

HRID 1065707 reaction equation
[CH:1]([N:3]([C@H:5]1[C@H:10]([OH:11])[CH2:9][C@H:8]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C:20]1[CH:19]=[CH:18][C:17]([OH:24])=[CH:16][C:15]=1[CH2:14][CH2:13]3)[CH3:4])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:4][N:3]([CH3:1])[C@H:5]1[C@H:10]([OH:11])[CH2:9][C@H:8]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C:20]1[CH:19]=[CH:18][C:17]([OH:24])=[CH:16][C:15]=1[CH2:14][CH2:13]3

Participants

4

Reactant 2

HCID 12961991HCID 12961991, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12961993HCID 12961993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 17β-(N-formyl-N-methylamino)-oestra-1,3,5(10)-triene-3,16α-diol (5.41 g) in tetrahydrofuran (110 ml) was kept at 10° C., while lithium aluminium hydride (5.41 g) was added portionwise. The resultant mixture was refluxed for 5 h., then the excess of lithium aluminium hydride was destroyed by careful addition of water. The mixture was diluted with a 1:1 mixture of tetrahydrofuran-ethylacetate (500 ml) and refluxed for 3 h. The inorganic salts were filtered off and washed with tetrahydrofuran-ethylacetate (500 ml; 1:1) and the filtrate was evaporated to dryness. The resultant crude product was crystallised from dichloromethane-methanol to give pure 17β-dimethylamino-oestra-1,3,5(10)-triene-3,16α-diol as an amorphous solid (3.83 g; 73.9%), m.p. 240°-242° C., [α]D +43.4° (c 1.33 in pyridine).

Workup

  1. additionwas added portionwise
  2. customthe excess of lithium aluminium hydride was destroyed by careful addition of water
  3. additionThe mixture was diluted with a 1:1 mixture of tetrahydrofuran-ethylacetate (500 ml)
  4. temperaturerefluxed for 3 h
  5. filtrationThe inorganic salts were filtered off
  6. washwashed with tetrahydrofuran-ethylacetate (500 ml; 1:1)
  7. customthe filtrate was evaporated to dryness
  8. customThe resultant crude product was crystallised from dichloromethane-methanol

Sources & evidence

ORD record
ord-7cd463de99f8486db711aab8b5002468
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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