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1,2-Dichloroethane → 2-Methyl-3-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one

HRID 2213559
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HRID 2213559 반응식
[CH3:1][C:2]1[NH:6][C:5]2[C:7](=[O:10])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([OH:13])=O.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>CN(C=O)C>[CH3:1][C:2]1[NH:6][C:5]2[C:7](=[O:10])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 219575932-Methyl-6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-3-carboxylic acid

생성물 1

HCID 586978542-Methyl-3-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one수율 81%

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-methyl-6-oxo-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid (Example B, 3.58 g, 20 mmol), HOBt (2.7 g, 20 mmol) and EDC (5.74 g, 30 mmol) in dry DMF (50 mL) was stirred at 0° C. to room temperature for 20 min. Then (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (24 mmol) was added and stirring was continued for 48 hours. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc, washed with sat. Na2CO3, dried, concentrated and purified on a silica gel column to give 5.1 g (81%) of the titled compound as a yellowish foam.

후처리

  1. stirringstirring
  2. waitwas continued for 48 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with sat. Na2CO3
  6. customdried
  7. concentrationconcentrated
  8. custompurified on a silica gel column

출처 및 근거

ORD 기록
ord-159715445ea846159869f66922c4f0fc
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07105562B2

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