HRID1014972

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID17587

N,N-Dimethylacrylamide

C5H9NO

HCID24758

Sodium hydride

HNa

结构：CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1

HCID67301438

未命名化合物

PRODUCTS

生成物

结构：CN(C)C(=O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C

HCID67301232

未命名化合物

收率 93.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (951 mg, 1.75 mmol) was treated with N,N-dimethylacrylamide (540 mg, 5.44 mmol) and sodium hydride (60% in oil, 105 mg, 2.62 mmol) in tetrahydrofuran (17.5 ml) in the same manner as shown in Example 4(1) (at 5° C. for 14 hours), followed by work up and purification using column chromatography (hexane:ethyl acetate= 2:1) to give the titled compound (1.05 g, 92.7%) as a yellow oil.

WORKUP

后处理

customas shown in Example 4(1) (at 5° C. for 14 hours)
custompurification

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b6806523fd05424d94c51e6cad121bc5
来源数据集: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07985744B2
来源说明: uspto-grants-2011_07

反应 SMILES

[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28][OH:29])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:38][N:39]([CH3:44])[C:40](=[O:43])[CH:41]=[CH2:42].[H-].[Na+]>O1CCCC1>[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28][O:29][CH2:42][CH2:41][C:40]([N:39]([CH3:44])[CH3:38])=[O:43])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]