Aluminium lithium hydride → [5-(2,2-Dimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]carbamic acid tert-butyl ester

HRID 1189829

반응식

HRID 1189829 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12](=[O:30])[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[CH2:26][CH2:25][NH:24][C:23](=O)[C:22]2([CH3:29])[CH3:28])=[CH:16][N:15]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12](=[O:30])[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[CH2:26][CH2:25][NH:24][CH2:23][C:22]2([CH3:29])[CH3:28])=[CH:16][N:15]=1)([CH3:10])([CH3:8])[CH3:9]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 66914612[5-(2,2-Dimethyl-3-oxo-piperazin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 66914635[5-(2,2-Dimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]carbamic acid tert-butyl ester수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

LiAlH4 (1M in THF, 78 mL, 78 mmol, 2 equiv) was added to a solution of [5-(2,2-dimethyl-3-oxo-piperazin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (Step 109.4) (13 g, 39 mmol) in THF (150 mL) at 50° C., under an argon atmosphere. The resulting mixture was stirred for 3 h at 50° C., cooled to 0° C., quenched by addition of acetone, filtered through a pad of celite and the filtrate was concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 97.5:1.5:1) to afford 7.25 g of the title compound as a white solid. Title compound: ESI-MS: 321.3 [M+H]+; tR=1.91 min (System 1); TLC: Rf=0.11 (DCM/MeOH, 9:1).

후처리

  1. temperaturecooled to 0° C.
  2. customquenched by addition of acetone
  3. filtrationfiltered through a pad of celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 97.5:1.5:1)

출처 및 근거

ORD 기록
ord-e27bb2f8444e4d39b1e7d9e4592964a7
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674099B2

연결된 노트

불러오는 중…