HRID2057295

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2724141

Tetra-n-butylammonium fluoride

C16H36FN

结构：CCN(CCCCC[C@H]1CC[C@H]([N+](C)([O-])S(=O)(=O)c2ccc(C(F)(F)F)cc2)CC1)CCO[Si](C)(C)C(C)(C)C

HCID178463969

未命名化合物

PRODUCTS

生成物

结构：CCN(CCO)CCCCC[C@H]1CC[C@H]([N+](C)([O-])S(=O)(=O)c2ccc(C(F)(F)F)cc2)CC1

HCID178464454

未命名化合物

收率 44%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

To 335 mg (5.5 mmol) trans-N-[4-(5-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide N-oxide in 8 ml THF were added 0.83 ml 1M TBAF at 0° C. The solution was stirred at RT for 1 h, partitioned between EtOAc and an aqueous solution of Na2CO3. The organic phase was washed with brine and dried over Na2SO4. Column chromatography with CH2Cl2/MeOH 9:1 yielded 190 mg (44%, 3 steps) trans-N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide N-oxide as colorless oil, MS: 495 (MH+).

WORKUP

后处理

custompartitioned between EtOAc
washThe organic phase was washed with brine
dry with materialdried over Na2SO4

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3bc60bece80d4de994b3bb15ce6531d6
来源数据集: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07335687B2
来源说明: uspto-grants-2008_02

反应 SMILES

C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH2:37][CH3:38])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([N+:21]([O-:36])([CH3:35])[S:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:17][CH2:16]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:37]([N:9]([CH2:8][CH2:7][OH:6])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([N+:21]([O-:36])([CH3:35])[S:22]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=2)(=[O:23])=[O:24])[CH2:17][CH2:16]1)[CH3:38]