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

HRID 43143

反応式

HRID 43143 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8d5fa18d3c42489f8e94966228da73ea
出典データセット
uspto-grants-2013_09
特許番号
US08536175B2

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