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HRID1920148

反应详情

EQUATION

反应方程式

HRID 1920148 的结构方程式

REACTANTS

反应物

3
结构：c1c[nH]cn1
HCID795

Imidazole

C3H4N2

结构：CC(C)(C)[Si](C)(C)Cl
HCID28928

Chloro(1,1-dimethylethyl)dimethylsilane

C6H15ClSi

结构：CC(C)(C)OC(=O)N[C@@H]1CN(C(=O)OCc2ccccc2)CC[C@H]1O
HCID53487823

Benzyl (3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxypiperidine-1-carboxylate

C18H26N2O5

PRODUCTS

生成物

1
结构：CC(C)(C)OC(=O)N[C@@H]1CN(C(=O)OCc2ccccc2)CC[C@H]1O[Si](C)(C)C(C)(C)C
HCID59455668

未命名化合物

收率 76%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

2 次

PROCEDURE

实验过程

To a solution of (3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylate (1.0 equiv.) in dichloromethane (0.1 M solution) was added imidazole (1.1 equiv.), DMAP (0.1 equiv.), and TBDMSCl (1.1 equiv.) sequentially. The reaction mixture was stirred at room temperature for 20 h. After worked up with dichloromethane, the crude material was purified by silica column chromatography (10% to 20% EtOAc in hexanes) yielding (3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate (76%). LCMS (m/z): 365.2 [(M-Boc)H+]; LC Rt=6.05 min.

WORKUP

后处理

  1. customthe crude material was purified by silica column chromatography (10% to 20% EtOAc in hexanes)