tert-Butyl (2S)-2-isopropyl-4-oxopyrrolidine-1-carboxylate → tert-butyl (2S)-4-hydroxy-4-methyl-2-(propan-2-yl)pyrrolidine-1-carboxylate

HRID 1852738ノート

反応式

HRID 1852738 の反応式
[O:1]=[C:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([CH:14]([CH3:16])[CH3:15])[CH2:3]1.[CH3:17][Mg]Br>C1COCC1>[OH:1][C:2]1([CH3:17])[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8])[C@H:4]([CH:14]([CH3:16])[CH3:15])[CH2:3]1

参加物

4

反応物 2

HCID 26967714tert-Butyl (2S)-2-isopropyl-4-oxopyrrolidine-1-carboxylateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 86724491tert-butyl (2S)-4-hydroxy-4-methyl-2-(propan-2-yl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of tert-butyl (2S)-4-oxo-2-(propan-2-yl)pyrrolidine-1-carboxylate (500 mg, 2.2 mmol) in THF (10 mL) at −78° C. was added methylmagnesium bromide (1.65 mL, 4.95 mmol) dropwise. The reaction was stirred at −78° C. for 2 hours before warming to room temperature and stirring for an additional 2 hours. The reaction was quenched by slowly adding saturated aqueous ammonium chloride at 0° C. The mixture was acidified with HCl (1N) and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-80% ethylacete/hexanes, linear gradient) to afford tert-butyl (2S)-4-hydroxy-4-methyl-2-(propan-2-yl)pyrrolidine-1-carboxylate.

後処理

  1. temperaturebefore warming to room temperature
  2. stirringstirring for an additional 2 hours
  3. customThe reaction was quenched by slowly adding saturated aqueous ammonium chloride at 0° C
  4. extractionextracted with ethyl acetate (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (0-80% ethylacete/hexanes, linear gradient)

出典と根拠

ORDレコード
ord-48c07e5b1867493d86eb59e0524d2e94
出典データセット
uspto-grants-2015_02
特許番号
US08962611B2

反応ノート

読み込み中…