Sodium Bicarbonate → METHYL 1-(3-methoxypropyl)indoline-6-carboxylate

HRID 922442ノート

反応式

HRID 922442 の反応式
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH:8]=[CH:7]1.[Na].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH2:8][CH2:7]1

参加物

5

反応物 3

HCID 516892Sodium Bicarbonate2 回HCID 5360545SodiumHCID 67542758methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate

生成物 1

HCID 86707862METHYL 1-(3-methoxypropyl)indoline-6-carboxylate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a mixture of methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate (1.5 g) and sodium cyanohydroborate (1.61 g) was added acetic acid (15 mL) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added aqueous saturated sodium hydrogen carbonate solution under ice-cooling, and the mixture was neutralized by adding sodium hydrogen carbonate, and then extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=2/1) to give methyl 1-(3-methoxypropyl)indoline-6-carboxylate [REx(10-1)] (1.20) as a pale yellow oil.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-ca05ce8e204c426393431c2055c8f0a7
出典データセット
uspto-grants-2016_03
特許番号
US09278944B2

反応ノート

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