N-methyl-2-pyrrolidone → HCID 131724564, compound
Reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:27])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24]CI.[F:28][C:29]([C:34]([F:49])([F:48])[C:35]([F:47])([F:46])[C:36]([F:45])([F:44])[C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39])=[CH:30][CH2:31][NH:32][CH3:33].[CH3:50]N1CCCC1=O>>[F:28][C:29]([C:34]([F:48])([F:49])[C:35]([F:46])([F:47])[C:36]([F:44])([F:45])[C:37]([F:42])([F:43])[C:38]([F:39])([F:40])[F:41])=[CH:30][CH2:31][N:32]([CH3:50])[CH2:33][CH2:24][CH2:23][CH2:22][CH2:21][C@@H:11]1[CH2:10][C:9]2[CH:8]=[C:7]([OH:27])[CH:6]=[CH:5][C:4]=2[C@@H:3]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][C@@H:2]2[F:1])([CH3:18])[C:16](=[O:20])[CH2:15][CH2:14]1Participants
4
Conditions
- Temperature
- 80 °C
Procedure
880 mg of 11β-fluoro-3-hydroxy-7α-(5-iodopentyl)-estra-1,3,5(10)-trien-17-one and 2.23 g of (3,4,4,5,5,6,6,7,7,8,8,8-dodecafluor-oct-2-enyl)-methyl-amine are dissolved in 20 ml of N-methylpyrrolidone and stirred for 1 hour at a bath temperature of 80° C. After the reaction solution is cooled to room temperature, the batch is added to saturated common salt solution, extracted with diethyl ether, dried and concentrated by evaporation in a vacuum. 2.47 g of 7α-{5-[(3,4,4,5,5,6,6,7,7,8,8,8-dodecafluor-oct-2-enyl)-methyl-amino]-pentyl}-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained as a crude product, which is used without purification in the next stage.
Workup
- temperatureAfter the reaction solution is cooled to room temperature
- additionthe batch is added to saturated common salt solution
- extractionextracted with diethyl ether
- customdried
- concentrationconcentrated by evaporation in a vacuum
Sources & evidence
- ORD record
- ord-27c60bf166314345a20cb56e6fe76289
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780855B2
Reaction notes
Loading…