N-methyl-3-phenoxypropan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesized according to typical procedures C and D from 3-phenoxypropionic acid and methylamine. Synthesized

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesized according to typical procedures C and D from 3-phenoxypropionic acid and methylamine. Synthesized

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesized according to typical procedures C and D from 3-phenoxypropionic acid and methylamine. Synthesized

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.57 g of methylamine is condensed in a solution of 1.6 ml of 3-phenoxy-propylbromide in 15 ml of anhydrous tetrahydrofuran at −78° C., and it is stirred overnight at room temperature in a pressurized reactor. After the pressurized reactor was opened at −20° C., it is allowed to come to room temperature to allow excess methylamine to evaporate off. Then, the reaction solution is added to saturated sodium chloride solution, extracted with ether, dried on magnesium sulfate and concentrated by evaporation in a vacuum. 2.01 g of methyl-(3-phenoxy-propyl)-amine is obtained as a crude product, which is used without further purification in the next stage. was opened at −20° C. to come to room temperature to evaporate off Then, the reaction solution is added to saturated sodium chloride solution extracted with ether dried on magnesium sulfate concentrated by evaporation in a vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 486 mg of 11β-fluor-7α-(5-iodopentyl)-estra-1,3,5(10)-triene-3,17β-diol in 10 ml of 1-methyl-2-pyrrolidinone is stirred with 600 mg of methyl-(3-phenoxy-propyl)-amine for 3 hours at a bath temperature of 80° C. Then, the batch is added to saturated sodium chloride solution, extracted with ether, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with methylene chloride/methanol/ammonia. 443 mg of 11β-fluoro-7α-{5-[methyl-(3-phenoxy-propyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam [α]D=+47° (c=0.5 in CHCl3). extracted with ether dried on sodium sulfate concentrated by evaporation in a vacuum chromatographed on silica gel with methylene chloride/methanol/ammonia

Conditions: temp:0.00; pressure:0.00; stir: