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HRID2369985

反应详情

EQUATION

反应方程式

HRID 2369985 的结构方程式

REACTANTS

反应物

2
结构：CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1N
HCID1514390

tert-Butyl hydrogen (2-aminocyclohexyl)carbonimidate

C11H22N2O2

结构：CS(=O)(=O)OC1CCCN(c2ccc(-c3ncco3)cc2)C1
HCID86690208

未命名化合物

PRODUCTS

生成物

2
结构：CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1NC1CCCN(c2ccc(-c3ncco3)cc2)C1
HCID71233117

未命名化合物

结构：CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1NCC1CCCN1c1ccc(-c2ncco2)cc1
HCID86690209

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC#N
溶剂HCID6342

Acetonitrile

C2H3N

CONDITIONS

反应条件

温度
120 °C

PROCEDURE

实验过程

To a solution of 1-(4-(oxazol-2-yl)phenyl)piperidin-3-yl methanesulfonate (110 mg, 0.341 mmol) in acetonitrile (4 mL) was added tert-butyl (1R,2R)-2-aminocyclohexylcarbamate (110 mg, 0.512 mmol). The reaction was stirred in a microwave at 120° C. for 30 min. After this time, LC/MS showed two pairs of products formed. The reaction was concentrated. The residue was diluted with EtOAc and washed with water. EtOAc extracts were concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 50-100% EtOAc/Hex to give desired product tert-butyl (1R,2R)-2-((1-(4-(oxazol-2-yl)phenyl)pyrrolidin-2-yl)methylamino)cyclohexylcarbamate and the unwanted diastereomer, tert-butyl (1R,2S)-2-((1-(4-(oxazol-2-yl)phenyl)pyrrolidin-2-yl)methylamino)cyclohexylcarbamate (156 mg total) as a white foam.

WORKUP

后处理

  1. customformed
  2. concentrationThe reaction was concentrated
  3. additionThe residue was diluted with EtOAc
  4. washwashed with water
  5. concentrationEtOAc extracts were concentrated
  6. customThe resulting residue was purified
  7. washeluting with a gradient of 50-100% EtOAc/Hex