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1,2-Dichloroethane → 4-[(3RS,4SR)-3-[(SR)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 559306
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HRID 559306 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[Cl:38][C:39]1[CH:40]=[C:41]([CH:46]2[CH2:50][NH:49][CH2:48][CH:47]2[CH:51]([O:53][C:54]2[CH:61]=[CH:60][C:57]([C:58]#[N:59])=[CH:56][N:55]=2)[CH3:52])[CH:42]=[CH:43][C:44]=1[Cl:45]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([N:49]2[CH2:50][CH:46]([C:41]3[CH:42]=[CH:43][C:44]([Cl:45])=[C:39]([Cl:38])[CH:40]=3)[CH:47]([CH:51]([O:53][C:54]3[CH:61]=[CH:60][C:57]([C:58]#[N:59])=[CH:56][N:55]=3)[CH3:52])[CH2:48]2)=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 669997186-{(SR)-1-[(3RS,4SR)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

생성물 1

HCID 66999616
4-[(3RS,4SR)-3-[(SR)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-piperidine-1-carboxylic acid tert-butyl ester
수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (0.165 g, 0.72 mmol) in 20 mL of CH2Cl2 was added (0.14 g, 0.94 mmol) of EDC, (0.10 g, 0.94 mmol) of HOBt and Et3N (0.11 mL, 1.1 mmol). After one hour at RT, was added 6-{(SR)-1-[(3RS,4SR)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile (VII-B-2, 0.26 g, 0.72 mmol). The mixture was stirred at RT over night and then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated under vacuo. Column chromatography (SiO2, EtOAc/H, 1:1) yielded 0.29 g (91%) of the title compound as a white foam.

후처리

  1. additionpoured onto water
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under vacuo

출처 및 근거

ORD 기록
ord-8dd2d4807462497498215635fed3d47f
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063075B2

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