Sodium Thiosulfate → tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

HRID 81111ノート

反応式

HRID 81111 の反応式
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH:5]12[O:22][CH:4]1[CH2:3][CH2:2][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6]2

参加物

5

反応物 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

生成物 1

HCID 21991116tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl 3,6-dihydropyridine-1(2H)-carboxylate (617 g, 3.37 mol) in anhydrous DCM (10 L) was added m-CPBA (989 g, 5.73 mol) in portions at 0° C. The mixture was stirred at room temperature for 1 hour. Saturated Na2S2O3 (1 L) was added and the organic layer was separated. The organic layer was washed with 5% aqueous K2CO3 (5 L×2), brine (4 L), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether:ethyl acetate=100:1-20:1) to obtain pure tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate.

後処理

  1. customthe organic layer was separated
  2. washThe organic layer was washed with 5% aqueous K2CO3 (5 L×2), brine (4 L)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (petroleum ether:ethyl acetate=100:1-20:1)

出典と根拠

ORDレコード
ord-d60bbda73a9a46f9b0e36b8c9cd27ab5
出典データセット
uspto-grants-2014_09
特許番号
US08846657B2

反応ノート

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