Hydrochloric Acid → 2-methyl-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one

HRID 526310

反応式

HRID 526310 の反応式
[CH3:1][NH:2][C:3](=O)[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:14]([O:16]CC)=O.[BH4-].[Na+].II.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:7]=[C:6]2[C:14]1=[O:16]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 89601817ethyl 1-(2-(methylamino)-2-oxoethyl)-1H-indole-2-carboxylate

生成物 1

HCID 578734942-methyl-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one収率 31.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a mixture of ethyl 1-(2-(methylamino)-2-oxoethyl)-1H-indole-2-carboxylate (0.86 g), NaBH4 (0.39 g) in 33 mL of THF stirred at 0° C. under a N2 atmosphere, a solution of Iodine (1.26 g, 10 mL THF) was added dropwise. The resulting mixture was reacted at 65° C. for 24 hr. The reaction was worked up by the addition of HCl (con., 1.5 mL) and heated at 65° C. for 4 hr. Then the mixture was neutralized by saturated NaHCO3 solution and the aqueous phase was extracted with EtOAc (2×60 mL). The combined organic phase was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by Combiflash (0-100% EtOAc/hexane) to afforded 208 mg of the title compound.

後処理

  1. customThe resulting mixture was reacted at 65° C. for 24 hr
  2. temperatureheated at 65° C. for 4 hr
  3. extractionthe aqueous phase was extracted with EtOAc (2×60 mL)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by Combiflash (0-100% EtOAc/hexane)

出典と根拠

ORDレコード
ord-fa0609ad5a1e4081a4aa69c3155c70a7
出典データセット
uspto-grants-2016_05
特許番号
US09345905B2

関連ノート

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