(R)-5-(3,4-difluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester → (2R,5S)-5-(3,4-difluorophenyl)pyrrolidine-2-carboxylic acid ethyl ester

HRID 1677082노트

반응식

HRID 1677082 반응식
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)=[N:7]1)=[O:5])[CH3:2]>[Pd].C(O)C>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C@@H:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)[NH:7]1)=[O:5])[CH3:2]

참가 물질

4

반응물 1

HCID 67371757(R)-5-(3,4-difluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester

생성물 1

HCID 67373516(2R,5S)-5-(3,4-difluorophenyl)pyrrolidine-2-carboxylic acid ethyl ester수율 72%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

10% palladium on carbon (1.2 g, 50% water content) was added to an ethanol (160 mL) solution of (R)-5-(3,4 difluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester (12.2 g), and under a hydrogen atmosphere, stirring was continued for 16 hours at room temperature. The catalyst was filtered on celite, and the filtrate was concentrated, and ethanol (160 mL) and 10% palladium on carbon (1.2 g, 50% water content) was again added to the residue, and under a hydrogen atmosphere, stirring was continued for 15 hours at room temperature. The catalyst was filtered on celite, and the filtrate was concentrated, and the residue was purified by silica gel column chromatography (heptane/ethyl acetate), and the title compound (8.86 g) was obtained. The physical property values are as follows.

후처리

  1. filtrationThe catalyst was filtered on celite
  2. concentrationthe filtrate was concentrated
  3. additionethanol (160 mL) and 10% palladium on carbon (1.2 g, 50% water content) was again added to the residue
  4. stirringunder a hydrogen atmosphere, stirring
  5. waitwas continued for 15 hours at room temperature
  6. filtrationThe catalyst was filtered on celite
  7. concentrationthe filtrate was concentrated
  8. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-fd50bd8c66a74147a32f365a53c1b5ab
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008293B2

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