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Cesium carbonate → 4-(5-Methoxymethyl-thieno[2,3-d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2111719
ノート
印刷プレビュー

反応式

HRID 2111719 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]([C:23]2[S:24][C:25]([CH2:29][O:30][CH3:31])=[CH:26][C:27]=2Br)=[N:21][OH:22])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>COCCO.[Cu](I)I>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[C:23]3[S:24][C:25]([CH2:29][O:30][CH3:31])=[CH:26][C:27]=3[O:22][N:21]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 10796Cesium carbonateHCID 724345774-[1-(3-Bromo-5-methoxymethyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 588176364-(5-Methoxymethyl-thieno[2,3-d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 80192-Methoxyethanol
溶媒

実験手順

Add cesium carbonate (1.13 g, 3.46 mmol, 1.50 equivalents) and copper iodide (44 mg, 0.23 mmol, 0.10 equivalents) to a stirred solution of 4-[1-(3-bromo-5-methoxymethyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester (1.00 g, 2.31 mmol, 1.00 equivalents) in 2-methoxy ethanol (23.30 mL). Stir the resulting mixture at room temperature overnight or up to 3 days and filter through celite. Evaporate the filtrate, partition the residue between ethyl acetate (70 mL) and water (23 mL) and separate. Extract the aqueous layer with ethyl acetate (3×70 mL), combine the organic layers, dry over magnesium sulfate, filter and evaporate. Purify the residue via flash column chromatography eluting with a mixture of hexane:ethyl acetate (4:1) to yield the desired product as a yellow oil. LC/MS (ESI), m/e 375 (MNa+), retention time 1.98 minutes. Condition II.

後処理

  1. waitup to 3 days
  2. filtrationfilter through celite
  3. customEvaporate the filtrate
  4. custompartition the residue between ethyl acetate (70 mL) and water (23 mL)
  5. customseparate
  6. extractionExtract the aqueous layer with ethyl acetate (3×70 mL)
  7. dry with materialdry over magnesium sulfate
  8. filtrationfilter
  9. customevaporate
  10. customPurify the residue via flash column chromatography
  11. washeluting with a mixture of hexane:ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-a7ebc92bd56a471ea7463cebfbb7914e
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07521445B2

反応ノート

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