Hydrochloric Acid → 7alpha-(9-Methylaminononyl)oestra-1,3,5(10)-triene-3,17beta-diol

HRID 543017Notes

Reaction equation

HRID 543017 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C@@H:11]([OH:20])[CH2:10][CH2:9]4)[C@H:6]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:31][CH3:32])=O)[CH2:5][C:4]=2[CH:3]=1.B.Cl>O1CCCC1>[CH3:32][NH:31][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C@@H:6]1[CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:19]=[CH:18][C:17]=2[C@@H:16]2[C@@H:7]1[C@H:8]1[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C@@H:11]([OH:20])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 704467659-(3,17beta-dihydroxyoestra-1,3,5(10)-trien-7alpha-yl)-N-methyl-nonanamide

Product 1

HCID 543355367alpha-(9-Methylaminononyl)oestra-1,3,5(10)-triene-3,17beta-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)-N-methylnonanamide (Example 27; 0.047 g.) and a molar solution of borane in tetrahydrofuran (5 ml.) was heated under reflux for 2 hours, cooled and concentrated aqueous hydrochloric acid (2 ml.) was added. The tetrahydrofuran was removed by evaporation and the residue was basified with aqueous 5N-sodium hydroxide solution and extracted three times with ethyl acetate (10 ml. each time). The combined extracts were washed with water (2 ml.), dried and evaporated to dryness. There was thus obtained as an oil 7α-(9-methylaminononyl)oestra-1,3,5(10)-triene-3,17β-diol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturecooled
  3. customThe tetrahydrofuran was removed by evaporation
  4. extractionextracted three times with ethyl acetate (10 ml
  5. washThe combined extracts were washed with water (2 ml.)
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-b92b1eca10c04c8d868dc302b01b0678
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

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