Sodium Bicarbonate → HCID 67312716、化合物

HRID 1010912ノート

反応式

HRID 1010912 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@@:12]1([CH3:19])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:14][CH2:13][C@:12]1([CH3:19])[CH2:16][CH2:17][CH2:18][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 18604408HCID 18604408、化合物

生成物 1

HCID 67312716HCID 67312716、化合物収率 62.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution obtained by dissolving 840 mg of the compound [63-1] in 16 mL of tetrahydrofuran, 4.31 mL of a borane-methyl sulfide complex (a 2 M tetrahydrofuran solution) was added at room temperature, and the mixture was heated under reflux for 4 hours. To the reaction solution, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 to 60/40) to obtain 498 mg of benzyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate [63-2] (hereinafter, referred to as the compound [63-2]).

後処理

  1. customTo a solution obtained
  2. additionwas added at room temperature
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 4 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe obtained organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe insolubles were filtered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 to 60/40)

出典と根拠

ORDレコード
ord-73b011ab4834440a968cb7c9d56dfd28
出典データセット
uspto-grants-2011_07
特許番号
US07977336B2

反応ノート

読み込み中…