Methanol → Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate

HRID 858921

반응식

HRID 858921 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[CH3:17]O>S(=O)(=O)(O)O.COC(OC)(C)C>[CH3:17][O:15][C:14]([CH:10]1[CH2:11][C:12](=[O:13])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[CH2:9]1)=[O:16]

참가 물질

5

반응물 2

HCID 887MethanolHCID 31453971-(4-Hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid

생성물 1

HCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate수율 84%

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매HCID 64952,2-Dimethoxypropane용매

실험 절차

The crude (RS)-1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid was dissolved in a mixture of 5000 ml of methanol, 24 ml of concentrated sulfuric acid and 400 ml of 2,2-dimethoxypropane and stirred under reflux for 2 h. The reaction solution was reduced to half of its volume by distillation, then transferred into a 20 l vessel. Under stirring at 40° C., a mixture of 2500 ml of water/ice (1:1) was added. Crystallisation started immediately, and, thereupon, the fine white crystals were collected on a filter funnel. They were washed with a total of 2000 ml of cold water until the filtrate was neutral. The product was dried under reduced pressure to yield 980 g (84% of theory, 2 steps) of (RS)-1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester as a white solid; MS: m/e=234 (M+H)+.

후처리

  1. temperatureunder reflux for 2 h
  2. distillationThe reaction solution was reduced to half of its volume by distillation
  3. customtransferred into a 20 l vessel
  4. stirringUnder stirring at 40° C.
  5. additiona mixture of 2500 ml of water/ice (1:1)
  6. additionwas added
  7. customCrystallisation
  8. customthe fine white crystals were collected on a filter funnel
  9. washThey were washed with a total of 2000 ml of cold water until the filtrate
  10. customThe product was dried under reduced pressure

출처 및 근거

ORD 기록
ord-8f13b1e3c76c4b1798e408009c9c2fad
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148362B2

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