Dimethyl Sulfide → 2-Cyclopropyl-1-(phenylmethyl)pyrrolidine

HRID 2367231ノート

反応式

HRID 2367231 の反応式
[CH:1]1([CH:4]2[N:8]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7](=O)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.S(C)C>C1COCC1>[CH:1]1([CH:4]2[CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 1068Dimethyl SulfideHCID 585044795-Cyclopropyl-1-(phenylmethyl)-2-pyrrolidinone

生成物 1

HCID 585044922-Cyclopropyl-1-(phenylmethyl)pyrrolidine収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

To 5-cyclopropyl-1-(phenylmethyl)-2-pyrrolidinone (240 mg, 1.12 mmol) in THF (5 mL) was added BH3.SMe2 2M in THF (5.6 mL, 11.2 mmol), and the reaction mixture was stirred over the weekend at room temperature. The reaction was quenched with the dropwise addition of CH3OH (˜2 mL, caution: vigorous H2 evolution occurs). The solution was poured onto water (˜50 mL) and EtOAc (˜50 mL), and the mixture was stirred at 60° C. for 3 hours. A saturated aqueous solution of NaHCO3 (˜25 mL) and EtOAc (˜50 mL) were added, and the organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% hexanes to 75% EtOAc/hexanes) afforded the title compound (100 mg, 45%) as a yellow oil. LC-MS (ES) m/z=202 [M+H]+.

後処理

  1. customThe reaction was quenched with the dropwise addition of CH3OH (˜2 mL, caution: vigorous H2 evolution occurs)
  2. additionThe solution was poured onto water (˜50 mL) and EtOAc (˜50 mL)
  3. additionA saturated aqueous solution of NaHCO3 (˜25 mL) and EtOAc (˜50 mL) were added
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-21ff3720f4dd4107b32cfaec033bea27
出典データセット
uspto-grants-2014_04
特許番号
US08697685B2

反応ノート

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