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

HRID 2367231노트

반응식

HRID 2367231 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 585044922-Cyclopropyl-1-(phenylmethyl)pyrrolidine수율 45%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-21ff3720f4dd4107b32cfaec033bea27
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

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