Potassium Carbonate → tert-Butyl 3-(acetylthio)pyrrolidine-1-carboxylate

HRID 2421965노트

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HRID 2421965 반응식
C(=O)([O-])[O-].[K+].[K+].[C:7]([OH:10])(=[S:9])[CH3:8].CS(O[CH:16]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1)(=O)=O>CO.CN(C=O)C.O>[C:7]([S:9][CH:20]1[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19]1)(=[O:10])[CH3:8]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylateHCID 178418634HCID 178418634, 화합물

생성물 1

HCID 54776232tert-Butyl 3-(acetylthio)pyrrolidine-1-carboxylate수율 24.2%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

Potassium carbonate (4.42 g, 31.96 mmol) was suspended in dry MeOH (20 mL) and thioacetic acid (2.28 g, 29.96 mmol) was added. The mixture was stirred vigorously for 10 mins, concentrated and diluted in dry DMF (30 mL). tert-Butyl 3-[(methylsulfonyl)oxy]pyrrolidine-1-carboxylate (2.65 g, 9.99 mmol) dissolved in dry DMF (20 mL) was added and the reaction mixture was heated to 60° C. for 3.5 h. The reaction mixture was diluted with water (350 mL) and extracted with EtOAc (2×150 mL) The organic phases were dried with MgSO4, filtered and evaporated. The crude product was purified using Biotage Horizon HPFC system (25+M column, isocratic run heptane/EtOAc (60:40)) affording the title compound (0.592 g, 24.2%) (the product is a mixture of cis and trans isomers). 1H NMR (500 MHz, CDCl3): δ 1.41 (d, 18H), 1.66 (d, 1H), 1.74-1.86 (m, 2H), 2.20-2.26 (m, 2H), 2.29 (s, 3H), 3.10-3.26 (m, 2H), 3.30-3.43 (m, 4H), 3.46-3.54 (m, 1H), 3.66-3.74 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 28.68, 30.82, 31.25, 32.34, 36.16, 41.09, 44.88, 51.60, 55.37, 79.67, 154.43; Mass Spectrum: M+H+ 241.

후처리

  1. concentrationconcentrated
  2. additiondiluted in dry DMF (30 mL)
  3. additionwas added
  4. extractionextracted with EtOAc (2×150 mL) The organic phases
  5. dry with materialwere dried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified

출처 및 근거

ORD 기록
ord-eb3cb61d2dcd42cea6efae5c13e9ac4d
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960380B2

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