氯化亚砜 → HCID 86672017，化合物

HRID 473835

反应方程式

HRID 473835 反应方程式
[OH:1][C:2]1([CH2:15][OH:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[S:26](Cl)(Cl)=[O:27].C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[O:1]1[C:2]2([CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3]2)[CH2:15][O:16][S:26]1=[O:27]

参与物

7

反应物 4

HCID 24386氯化亚砜HCID 81531N,N-二异丙基乙胺HCID 516892碳酸氢钠HCID 225945581-BOC-4-羟基-4-羟甲基哌啶

产物 1

HCID 86672017HCID 86672017，化合物收率 117.1%

试剂、催化剂与溶剂 2

HCID 8028四氢呋喃溶剂HCID 8857乙酸乙酯溶剂

实验过程

To a solution of tert-butyl 4-hydroxy-4-(hydroxymethyl)piperidine-1-carboxylate (Bioorganic & Medicinal Chemistry Letters 2008, 18(21), 5804-5808) (400 mg, 1.73 mmol) and DIPEA (1.2 mL, 7.0 mmol) in THF (10 mL) cooled to 0° C. was added thionyl chloride (0.65 mL, 8.6 mmol) in a dropwise manner and the mixture was stirred at this temperature for 1 h. The mixture was then partioned with saturated aqueous sodium bicarbonate and ethyl acetate. The organic phase was extracted with ethyl acetate (3×) and the combined organic layers were washed with brine then dried over anhydrous sodium sulfate, filtered and concentrated to afford 1,1-dimethylethyl 1,3-dioxa-2-thia-8-azaspiro[4.5]decane-8-carboxylate 2-oxide (562 mg) as an amber oil that was used without further purification. GC-MS (EI) for C11H19NO5S: 277 (M+).

后处理

  1. extractionThe organic phase was extracted with ethyl acetate (3×)
  2. washthe combined organic layers were washed with brine
  3. dry with materialthen dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

来源与证据

ORD记录
ord-85b80142be584187a5447049722724f0
来源数据集
uspto-grants-2014_01
专利号
US08637499B2

关联笔记

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