Sulfuric acid magnesium salt (1:1) → 4-[(Benzofuran-6-ylmethyl)-amino]-butyric acid ethyl ester

HRID 408590

反応式

HRID 408590 の反応式
Cl.[CH2:2]([O:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][NH2:9])[CH3:3].[O:11]1[C:15]2[CH:16]=[C:17]([CH:20]=O)[CH:18]=[CH:19][C:14]=2[CH:13]=[CH:12]1.[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C1COCC1.CO>[CH2:2]([O:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][NH:9][CH2:20][C:17]1[CH:18]=[CH:19][C:14]2[CH:13]=[CH:12][O:11][C:15]=2[CH:16]=1)[CH3:3]

参加物

7

反応物 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 14354086Benzofuran-6-carbaldehyde

生成物 1

HCID 705564744-[(Benzofuran-6-ylmethyl)-amino]-butyric acid ethyl ester

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

To a solution of 4-amino-butyric acid ethyl ester hydrochloride (1 eq.) in THF was added TEA (2.5 eq.). The mixture was stirred 5 min at 20° C., then benzofuran-6-carbaldehyde (0.95 eq.) and MgSO4 (3 eq.) were added. The reaction was refluxed for 2 h, then cooled to 20° C. and filtered. The filtrate was added to a suspension of NaBH4 (2 to 6 eq.) in MeOH at −15° C. The reaction was stirred for 2 h at −15° C. The reaction was quenched with the addition of aqueous HCl 2N until pH=2. The aqueous layer was washed twice with EtOAc. The organic layers were discarded. Solid KOH was added to the aqueous layer. The crude was extracted three times with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure at 20° C. The crude was purified by chromatography on silica gel (elution with DCM/MeOH: 95/5) to afford 4-[(benzofuran-6-ylmethyl)-amino]-butyric acid ethyl ester.

後処理

  1. temperatureThe reaction was refluxed for 2 h
  2. temperaturecooled to 20° C.
  3. filtrationfiltered
  4. stirringThe reaction was stirred for 2 h at −15° C
  5. customThe reaction was quenched with the addition of aqueous HCl 2N until pH=2
  6. washThe aqueous layer was washed twice with EtOAc
  7. additionSolid KOH was added to the aqueous layer
  8. extractionThe crude was extracted three times with EtOAc
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure at 20° C
  12. customThe crude was purified by chromatography on silica gel (elution with DCM/MeOH: 95/5)

出典と根拠

ORDレコード
ord-ac60bff47ab3460f836ac051f1ee32e2
出典データセット
uspto-grants-2014_06
特許番号
US08759334B2

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