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(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide → (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-pyrrolidin-3-yl]-2-piperidinecarboxamide

HRID 412636
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HRID 412636 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][C@@H:19]1[CH2:23][CH2:22][N:21](CC2C=CC=CC=2)[CH2:20]1)=[O:17]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:11]([NH:10][CH2:15][CH3:14])[CH3:12].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][C@@H:19]1[CH2:23][CH2:22][NH:21][CH2:20]1)=[O:17]
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참가 물질

5

반응물 1

HCID 57172017(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide

생성물 2

HCID 8021DiethylamineHCID 57279632(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-pyrrolidin-3-yl]-2-piperidinecarboxamide수율 4.1%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

20% w/w Palladium hydroxide on carbon (12.5 mg) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide (62.5 mg) [see Example 1] in ethanol (10 ml). The reaction mixture was hydrogenated at 414 kPa (60 p.s.i.) for 56 hours, after which time the catalyst was filtered off and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 95:5 changing to 90:10, by volume, ethyl acetate:diethylamine to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-pyrrolidin-3-yl]-2-piperidinecarboxamide (1 mg) as an oil.

후처리

  1. filtrationafter which time the catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 95:5 changing to 90:10, by volume, ethyl acetate

출처 및 근거

ORD 기록
ord-8d8333426cc843e784b9fed7037fdbf9
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06562964B1

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