Sodium hydride → 3-(S)-Amino-1-(4-Chloroquinolin-6-ylmethyl)-pyrrolidin-2-one hydrochloride

HRID 394605ノート

反応式

HRID 394605 の反応式
[H-].[Na+].C(OC(=O)[NH:9][C@H:10]1[CH2:14][CH2:13][NH:12][C:11]1=[O:15])(C)(C)C.Br[CH2:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][CH:23]=[C:22]2[Cl:29]>C1COCC1>[ClH:29].[NH2:9][C@H:10]1[CH2:14][CH2:13][N:12]([CH2:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[CH:24][CH:23]=[C:22]3[Cl:29])[C:11]1=[O:15]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10750535(S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamateHCID 149912836-(Bromomethyl)-4-chloroquinoline

生成物 1

HCID 206807203-(S)-Amino-1-(4-Chloroquinolin-6-ylmethyl)-pyrrolidin-2-one hydrochloride収率 143%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Sodium hydride (0.096 g, 2.4 mmol, 60% by weight) is added to a solution of [2-oxopyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester (0.4 g, 2 mmol) in 15 mL, of THF at 0° C. The mixture is stirred for 30 minutes then a solution of 6-bromomethyl-4-chloroquinoline (0.513 g, 2 mmol) in 15 mL THF is added slowly. The resulting solution is warmed to room temperature over 4 hours. The reaction mixture is quenched with saturated ammonium chloride solution then diluted with EtOAc. The organic layer is separated, washed with brine, dried over Na2SO4, filtered and concentrated. The residue is dissolved in ethyl acetate (50 mL), and saturated with HCl gas at 0° C. The solution is stirred at 0° C. for 15 minutes, then the solution is warmed to room temperature. After four hours at room temperature, the solid that precipitates is collected, and washed with ether to give the title compound (0.445 g, 1.43 mmol) as a pale yellow solid.

後処理

  1. customThe reaction mixture is quenched with saturated ammonium chloride solution
  2. additionthen diluted with EtOAc
  3. customThe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue is dissolved in ethyl acetate (50 mL)
  9. customat 0° C
  10. stirringThe solution is stirred at 0° C. for 15 minutes
  11. temperaturethe solution is warmed to room temperature
  12. waitAfter four hours at room temperature
  13. customthe solid that precipitates
  14. customis collected
  15. washwashed with ether

出典と根拠

ORDレコード
ord-e28dc5fb5c564c27b23ed5e967b22efe
出典データセット
uspto-grants-2003_08
特許番号
US06602864B1

反応ノート

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