Trifluoroacetic acid → Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate

HRID 1808338ノート

反応式

HRID 1808338 の反応式
FC(F)(F)C(O)=O.N1([C:13]23[O:28][N:27]=[C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:14]2[CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18]3)CCCC1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:28]1[C:13]2[CH2:18][CH2:17][NH:16][CH2:15][C:14]=2[C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:27]1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 685054785-tert-Butyl 3-ethyl 7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridine-3,5(6H)-dicarboxylate

生成物 1

HCID 44558551Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate収率 62%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Trifluoroacetic acid (6.67 ml, 89.9 mmol) was added at 0° C. to a solution of 5-tert-butyl 3-ethyl 7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridine-3,5(6H)-dicarboxylate (5.5 g, 14.98 mmol) in DCM (100 ml), and the mixture was stirred for 16 hours under reflux. Cooling to 0° C. was then carried out and NaHCO3 solution was added. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. Purification of the crude product was carried out by column chromatography (silica gel, 16% methanol in ethyl acetate). Yield: 62% [Alternatively, ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate A-06 can be synthesised as described in WO2006105945.]

後処理

  1. temperatureunder reflux
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude product
  8. customYield: 62% [Alternatively, ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate A-06 can be synthesised

出典と根拠

ORDレコード
ord-ad1b1b1750894bf6ae45824746de2b18
出典データセット
uspto-grants-2013_01
特許番号
US08357717B2

反応ノート

読み込み中…