(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → tert-butyl (S)-1-(2-((trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-ylcarbamate

HRID 535804노트

반응식

HRID 535804 반응식
Cl[CH2:2][CH2:3][NH:4][C@@H:5]1[CH2:7][C@H:6]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[CH:10][CH:9]=1.[NH:24]1[CH2:28][CH2:27][C@H:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25]1>CN(C=O)C>[F:21][C:20]([F:23])([F:22])[C:16]1[CH:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C@@H:6]3[CH2:7][C@H:5]3[NH:4][CH2:3][CH2:2][N:24]3[CH2:28][CH2:27][C@H:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:25]3)=[CH:9][CH:10]=2)[CH:19]=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 89123862(trans)-N-(2-chloroethyl)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropanamine

생성물 1

HCID 86673372tert-butyl (S)-1-(2-((trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-ylcarbamate수율 37%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (trans)-N-(2-chloroethyl)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropanamine (750 mg, 2.21 mmol) in dry DMF (7.5 mL), (S)-tert-butyl pyrrolidin-3-ylcarbamate (864 mg g, 4.64 mmol) was added and stirred at RT for 48 h. After completion, the reaction mixture was poured into ice water (25 mL), extracted with EtOAc (2×20 mL). The combined extracts were washed with water (25 mL), brine (20 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography (SiO2) using MeOH: CHCl3(4:96) to get tert-butyl (S)-1-(2-((trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-ylcarbamate (400 mg, 37%) as a white solid.

후처리

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined extracts were washed with water (25 mL), brine (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by column chromatography (SiO2)

출처 및 근거

ORD 기록
ord-8c29d5dc90f64551bb0ac83e0d7cfd57
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859555B2

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