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

HRID 922442노트

반응식

HRID 922442 반응식
[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

참가 물질

5

반응물 3

HCID 516892Sodium Bicarbonate2회HCID 5360545SodiumHCID 67542758methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ca05ce8e204c426393431c2055c8f0a7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278944B2

반응 노트

불러오는 중…