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HRID1948385

反应详情

EQUATION

反应方程式

HRID 1948385 的结构方程式

REACTANTS

反应物

3
结构：CCN(C(C)C)C(C)C
HCID81531

Diisopropylethylamine

C8H19N

结构：CC(C)(C)OC(=O)N1CCC(N)C(N=[N+]=[N-])C1
HCID72275737

未命名化合物

2 次

结构：Cc1[nH]c(C(=O)Cl)c(Cl)c1Cl
HCID86038394

3,4-Dichloro-5-methyl-1H-pyrrole-2-carbonyl chloride

C6H4Cl3NO

PRODUCTS

生成物

1
结构：Cc1[nH]c(C(=O)N[C@H]2CCN(C(=O)OC(C)(C)C)C[C@H]2N=[N+]=[N-])c(Cl)c1Cl
HCID131730339

未命名化合物

收率 69%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

2 次

PROCEDURE

实验过程

Crude tert-butyl-4-amino-3-azidopiperidine-1-carboxylate (Intermediate 270, 3.3 mmol) was dissolved in anhydrous CH2Cl2 (10 ml) and DIEA (1.27 g; 1.6 ml; 9.9 mmol; 3 eq.). The solution was cooled to 0 C and 3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl chloride (736 mg; 3.5 mmol; 1.05 eq.) was added. The reaction was complete within 30 minutes. Dilute with CH2Cl2 and wash with H2O (×2), brine and dried over Na2SO4. Filter and concentrate. Purify by flash column chromatography (0-60% EtOAc/hexanes). Isolation gave 967 mg in 69% yield over the two-step sequence. LC/MS (ES−)[(M−H)+]: 415, 417 for C16H22Cl2N6O3.

WORKUP

后处理

  1. additionwas added
  2. washwash with H2O (×2), brine
  3. dry with materialdried over Na2SO4
  4. filtrationFilter
  5. concentrationconcentrate
  6. customPurify by flash column chromatography (0-60% EtOAc/hexanes)
  7. customIsolation gave 967 mg in 69% yield over the two-step sequence