HRID1837243

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID5234

Sodium chloride

ClNa

HCID17910986

未命名化合物

结构：C[C@]12C[C@H](F)[C@@H]3c4ccc(O)cc4C[C@@H](CCCCCBr)[C@H]3[C@@H]1CCC2O

HCID69918048

未命名化合物

PRODUCTS

生成物

结构：CN(CCCCCCC(F)(F)C(F)(F)F)CCCCC[C@@H]1Cc2cc(O)ccc2[C@@H]2[C@@H]1[C@@H]1CC[C@H](O)[C@@]1(C)C[C@@H]2F

HCID15858653

未命名化合物

收率 94.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID13387

N-Methyl-2-pyrrolidone

C5H9NO

PROCEDURE

实验过程

A solution of 466 mg of 7α-(5-bromopentyl)-11β-fluor-estra-1,3,5(10)-triene-3,17-diol in 10 ml of 1-methyl-2-pyrrolidinone is stirred with 702 mg of methyl-(7,7,8,8,8-pentafluor-octyl)-amine for 3 hours at a bath temperature of 80° C. For working-up, the batch is added to saturated sodium chloride solution, extracted with ethyl acetate, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane/methanol. 595 mg of 11β-fluoro-7α-{5-[methyl-(7,7,8,8,8-pentafluor-octyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam, [α]D=+39° (c=0.5 in CHCl3).

WORKUP

后处理

extractionextracted with ethyl acetate
customdried on sodium sulfate
concentrationconcentrated by evaporation in a vacuum
customchromatographed on silica gel with dichloromethane/methanol

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cd48ba1e5bbf41af8922c0e0e60aa721
来源数据集: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06780855B2
来源说明: uspto-grants-2004_08

反应 SMILES

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[CH:12]([OH:27])[CH2:11][CH2:10]1.[CH3:28][NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([F:42])([F:41])[C:37]([F:40])([F:39])[F:38].[Cl-].[Na+]>CN1CCCC1=O>[F:26][C@H:16]1[CH2:15][C@@:13]2([CH3:14])[C@@H:9]([CH2:10][CH2:11][C@@H:12]2[OH:27])[C@H:8]2[C@H:17]1[C:18]1[CH:19]=[CH:20][C:21]([OH:25])=[CH:22][C:23]=1[CH2:24][C@H:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:29]([CH3:28])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([F:41])([F:42])[C:37]([F:38])([F:39])[F:40]