1,2-Diaminocyclohexane, trans- → (S)-tert-butyl 4-(3-(6-(methylsulfonyl)pyridin-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

HRID 407947노트

반응식

HRID 407947 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@H:16]([O:19][C:20]3[CH:21]=[N:22][C:23](Br)=[CH:24][CH:25]=3)[C:15]2=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:28]([S:30]([O-:32])=[O:31])C.[Na+].[C@@H]1(N)CCCC[C@H]1N>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@H:16]([O:19][C:20]3[CH:21]=[N:22][C:23]([S:30]([CH3:28])(=[O:32])=[O:31])=[CH:24][CH:25]=3)[C:15]2=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 438061,2-Diaminocyclohexane, trans-HCID 22986214Sodium EthanesulfinateHCID 86688100(S)-tert-butyl-4-(3-(6-bromopyridin-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

생성물 1

HCID 66800509(S)-tert-butyl 4-(3-(6-(methylsulfonyl)pyridin-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate수율 100.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
110 °C

실험 절차

A solution of (S)-tert-butyl-4-(3-(6-bromopyridin-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (315 mg, 0.714 mmol) in degassed DMSO (5 mL) was added sodium ethanesulfinate (117 mg, 1.15 mmol), trans-cyclohexane-1,2-diamine (33 mg, 0.286 mmol) and Cu(I) triflate benzene complex (54 mg, 0.107 mmol). The reaction was heated to 110° C. for 12 hours at which point the reaction was cooled to ambient temperature and partitioned between water (5 mL) and EtOAc (10 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×5 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The resulting material was purified by silica gel chromatography eluting with 1:1 hexanes/EtOAc to yield (S)-tert-butyl-4-(3-(6-(methylsulfonyl)pyridine-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (315 mg, 94%) as a white solid.

후처리

  1. temperaturewas cooled to ambient temperature
  2. custompartitioned between water (5 mL) and EtOAc (10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with EtOAc (2×5 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting material was purified by silica gel chromatography
  9. washeluting with 1:1 hexanes/EtOAc

출처 및 근거

ORD 기록
ord-f454c60ea7bc4b48aeb6febbd74047c9
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754226B2

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