Benzyl chloroformate → benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate

HRID 517559노트

반응식

HRID 517559 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:10]=1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>CO.[OH-].[Na+]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:17][CH2:16]2)[CH:10]=1

참가 물질

5

반응물 2

HCID 10387Benzyl chloroformateHCID 867114981-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine

생성물 1

HCID 86711499benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate수율 58%

시약·촉매·용매 2

HCID 887Methanol용매HCID 14798Sodium Hydroxide용매

실험 절차

To a solution of 1-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine (8.5 g, 30.6 mmol) in MeOH (30 mL), NaOH (2 M, 31 mL) was slowly added at RT, followed by the addition of benzyl chloroformate (6.4 g, 37 mmol) in portions at 0° C. The mixture was stirred at RT overnight. The solution was concentrated and diluted with H2O (500 mL), extracted with EtOAc (3×200 mL). The combined organic layers were washed with H2O (100 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by silica gel column chromatography (Petroleum ether:EtOAc=1:1) to afford benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate as a yellow oil (7.3 g, 58%). MS (ES+) C23H29N3O4 requires: 411, found: 412[M+H]+.

후처리

  1. concentrationThe solution was concentrated
  2. additiondiluted with H2O (500 mL)
  3. extractionextracted with EtOAc (3×200 mL)
  4. washThe combined organic layers were washed with H2O (100 mL) and brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the crude product, which
  9. customwas purified by silica gel column chromatography (Petroleum ether:EtOAc=1:1)

출처 및 근거

ORD 기록
ord-700a54ea03bc4284ade81f11679fbda5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115120B2

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