Triacetoxyperiodinane → Tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate

HRID 1749986ノート

反応式

HRID 1749986 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[CH:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

生成物 1

HCID 10657745Tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate収率 88.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of tert-butyl 4-(3-hydroxypropyl)piperidine-1-carboxylate (1.00 g, 4.11 mmol) in methylene chloride (20 mL) was cooled to 0° C., and added with the Dess-Martin reagent (2.27 g, 5.34 mmol), and then the mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered, and the filtrate was washed with saturated aqueous sodium hydrogencarbonate, and then further washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate (0.874 g, 88%).

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with saturated aqueous sodium hydrogencarbonate
  3. washfurther washed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-8ada52b783d14dfdac81c0773a41f46c
出典データセット
uspto-grants-2015_10
特許番号
US09156827B2

反応ノート

読み込み中…