Hydrochloric Acid → (1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanol

HRID 248888노트

반응식

HRID 248888 반응식
[F:1][C:2]([F:5])([F:4])I.[CH2:6]([N:13]([CH3:27])[C:14]([CH2:16][CH2:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH:25]=[O:26])=[O:19])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl>[Zn].CN(C=O)C>[CH2:6]([N:13]([CH3:27])[C:14]([CH2:16][CH2:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH:25]([OH:26])[C:2]([F:5])([F:4])[F:1])=[O:19])=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 16843TrifluoroiodomethaneHCID 14674666(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-al

생성물 1

HCID 14995339(1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanol수율 24.8%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 6228Dimethylformamide용매

실험 절차

Trifluoroiodomethane (2.3 g) was cooled to -78° C. with a trap. DMF (7 ml), (2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-al (710 mg) and zinc (1.0 g) were added there to. And the mixture was treated with ultrasonic waves for 2 hrs. at room temperature. 1N hydrochloric acid was added to the reaction solution. The mixture was extracted with EtOAc. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (217 mg) having the following physical data:

후처리

  1. additionAnd the mixture was treated with ultrasonic waves for 2 hrs
  2. customat room temperature
  3. extractionThe mixture was extracted with EtOAc
  4. washThe extract was washed
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

출처 및 근거

ORD 기록
ord-45d7cb3e577943959cd79a7f8d380ef0
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212191

반응 노트

불러오는 중…