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(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → (S)-tert-butyl (1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)carbamate

HRID 1755229
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HRID 1755229 반응식
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.Cl[C:15]1[C:16]2[N:17]([CH:21]=[CH:22][N:23]=2)[CH:18]=[CH:19][N:20]=1>C(NC(C)C)(C)C.CN1C(=O)CCC1.C(OCC)(=O)C>[N:23]1[CH:22]=[CH:21][N:17]2[CH:18]=[CH:19][N:20]=[C:15]([N:1]3[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]3)[C:16]=12
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참가 물질

6

반응물 2

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 102612868-Chloroimidazo[1,2-a]pyrazine

생성물 1

HCID 75204083(S)-tert-butyl (1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)carbamate수율 94.9%

시약·촉매·용매 3

HCID 7912Diisopropylamine용매HCID 8857Ethyl Acetate용매
HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
100 °C

실험 절차

To a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (80.2 g, 0.43 mol, 1.1 eq) in 75 mL of diisopropylamine and 34 mL of NMP was added portionwise 8-chloroimidazo[1,2-a]pyrazine (60 g, 0.39 mol, 1 eq). The reaction mixture was heated at 100° C. for 4 h and was then diluted with 1.2 L of ethyl acetate. The organic layer was washed with H2O and brine, dried with Na2SO4 and concentrated to give (S)-tert-butyl (1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)carbamate (111.7 g, 0.37 mol, 94%).

후처리

  1. washThe organic layer was washed with H2O and brine
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f3496f511a3049b697373ccff98be8b4
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09169261B2

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