3-Bromoquinoline → (5-Oxo-5-quinolin-3-yl-pentyl)-carbamic acid tert-butyl ester

HRID 379261ノート

反応式

HRID 379261 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Li]CCCC.[C:17]([O:21][C:22](=[O:34])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](=[O:33])N(OC)C)([CH3:20])([CH3:19])[CH3:18]>C(OCC)C>[C:17]([O:21][C:22](=[O:34])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](=[O:33])[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)([CH3:20])([CH3:18])[CH3:19]

参加物

5

反応物 3

HCID 214133-BromoquinolineHCID 17958956Tert-butyl (5-(methoxy(methyl)amino)-5-oxopentyl)carbamateHCID 178418339Butyllithium

生成物 1

HCID 53998977(5-Oxo-5-quinolin-3-yl-pentyl)-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a stirred solution of 3-bromoquinoline (25 g, 120 mmol) in diethyl ether −78° C. was added nBuLi (2.5M THF, 48 ml, 120 mmol) dropwise over 30 minutes. After 30 minutes, 21-2 (3.9 g, 15 mmol), dissolved in 50 ml ether was added dropwise over 10 minutes. After 30 minutes, the cooling bath was removed. After 1.0 hour, the reaction was quenched with sat. NH4Cl. The organic portion was separated, washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel, 20-50% ethyl acetate/hexanes) to give 21-3 as a yellow solid.

後処理

  1. additionwas added dropwise over 10 minutes
  2. waitAfter 30 minutes
  3. customthe cooling bath was removed
  4. waitAfter 1.0 hour
  5. customthe reaction was quenched with sat. NH4Cl
  6. customThe organic portion was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was chromatographed (silica gel, 20-50% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-7e27a5bedc724256b7f8397a83595144
出典データセット
uspto-grants-2001_10
特許番号
US06297249B1

反応ノート

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