HRID1837246

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](CCCCCCI)[C@H]3[C@@H]1CCC2O

HCID69917772

未命名化合物

PRODUCTS

生成物

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

HCID15870659

未命名化合物

收率 69%

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 690 mg of 11β-fluor-7α-(6-iodohexyl)-estra-1,3,5(10)-triene-3,17-diol in 15 ml of 1-methyl-2-pyrrolidinone is stirred with 810 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 ether, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane/methanol/ammonia (25%). 576 mg of 11β-fluoro-7α-{6-[methyl-(7,7,8,8,8-pentafluor-octyl)-amino]-hexyl}-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam, [α]D=+42° (c=0.5 in CHCl3).

WORKUP

后处理

extractionextracted with ether
customdried on sodium sulfate
concentrationconcentrated by evaporation in a vacuum
customchromatographed on silica gel with dichloromethane/methanol/ammonia (25%)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1c7fa8314ec34c0ca45031564f43754b
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

[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][CH:16]2[OH:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]I.[CH3:29][NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39].[Cl-].[Na+]>CN1CCCC1=O>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:30]([CH3:29])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([F:42])([F:43])[C:38]([F:39])([F:40])[F:41]