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Acetic Acid → (2S)-1-({(1S)-2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indole-1-yl]-1-methyl-ethylamino}-acetyl)-pyrrolidine-2-carbonitrile

HRID 982840
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HRID 982840 반응식
C(OC(=O)[NH:7][C@@H:8]([CH3:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:17]=2)[CH:12]=[CH:11]1)(C)(C)C.C(Cl)Cl.[BH3-][C:33]#[N:34].[Na+].[C:36]([OH:39])(=O)[CH3:37]>C(OCC)(=O)C>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:17]=[C:18]3[C:13]([CH2:12][CH2:11][N:10]3[CH2:9][C@@H:8]([NH:7][CH2:37][C:36]([N:10]3[CH2:18][CH2:13][CH2:12][C@H:11]3[C:33]#[N:34])=[O:39])[CH3:27])=[CH:14][CH:15]=2)=[CH:24][CH:23]=1
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 67031552(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester

생성물 1

HCID 66762315(2S)-1-({(1S)-2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indole-1-yl]-1-methyl-ethylamino}-acetyl)-pyrrolidine-2-carbonitrile

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester (1.80 g) was dissolved in acetic acid (25 mL) and CH2Cl2 (10 mL) and cooled to 0° C. NaCNBH3 (1.41 g) was added in portions and the resulting mixture was allowed to stir for 4 hours. The reaction mixture was diluted with ethyl acetate and extracted with concentrated NaOH solution. The organic layer was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (gradient of ethyl acetate in hexanes) to give the title compound as a brown oil (1.7 g).

후처리

  1. extractionextracted with concentrated NaOH solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (gradient of ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-20e9ccfa55804e2bb98301e40343df5b
출처 데이터셋
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06861440B2

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