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HRID1666529

反应详情

EQUATION

反应方程式

HRID 1666529 的结构方程式

REACTANTS

反应物

2
结构：CCCCS
HCID8012

1-Butanethiol

C4H10S

结构：COC(=O)[C@@H]1C[C@@](O)(c2ccc(-c3ccccc3)cc2)CN1C(=O)OCc1ccccc1
HCID59386561

未命名化合物

PRODUCTS

生成物

1
结构：CCCCS[C@]1(c2ccc(-c3ccccc3)cc2)C[C@@H](C(=O)OC)N(C(=O)OCc2ccccc2)C1
HCID57988328

未命名化合物

收率 43.3%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：O=S(=O)([O-])C(F)(F)F.O=S(=O)([O-])C(F)(F)F.O=S(=O)([O-])C(F)(F)F.[Sc+3]
催化剂HCID2734571

Scandium(III) triflate

C3F9O9S3Sc

结构：CC#N
溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

To a clear solution of (2S,4R)-1-benzyl 2-methyl 4-(biphenyl-4-yl)-4-hydroxypyrrolidine-1,2-dicarboxylate (2.59 g, 6 mmol) and 1-butanethiol (0.773 mL, 7.20 mmol) in acetonitrile (30 mL) was added Scandium(III) trifluoromethanesulfonate (0.295 g, 0.600 mmol) as solid by one portion at room temperature. The formed pink solution was stirred at this temperature for 26 hours. TLC analysis showed starting material was completely consumed. Quenched with saturated ammonium chloride, extracted with ethyl acetate. Washed the organic phase with brine, dried over MgSO4, filtered, concentrated in vacuo. The residue was purified by BIOTAGE® column, eluted with gradient 5˜40% ethyl acetate-hexane to afford the mixture of diastereomers 2.54 g (84%). This oily mixture was purified by BIOTAGE® again, eluted with gradient 0˜20% ethyl acetate-toluene. The first peak collected from the column afforded by-product (2S,4S)-1-benzyl 2-methyl 4-(biphenyl-4-yl)-4-(butylthio)pyrrolidine-1,2-dicarboxylate (1.54 g, 2.60 mmol, 43.3% yield) as a wax. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 0.77 (t, J=7.17, 3H), 1.21-1.24 (m, 2 H), 1.28-1.34 (m, 2 H), 2.20-2.29 (m, 2 H), 2.41-2.46 (m, 1 H), 2.86 (dd, J=12.82, 7.32 Hz, 1 H), 3.53, 3.75 (s, rotomer, 3 H), 3.89 (dd, J=17.09, 11.29 Hz, 1 H), 4.23-4.36 (m, 1 H), 4.69-4.77 (m, 1 H) 5.22-5.30 (m, 2 H) 7.28-7.44 (m, 10 H), 7.53-7.60 (m, 4 H). LC-MS (retention time: 3.28 min, method B), MS m/z 504 (M+H).

WORKUP

后处理

  1. customwas completely consumed
  2. customQuenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washWashed the organic phase with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by BIOTAGE® column
  9. washeluted with gradient 5˜40% ethyl acetate-hexane
  10. customto afford
  11. additionthe mixture of diastereomers 2.54 g (84%)
  12. customThis oily mixture was purified by BIOTAGE® again
  13. washeluted with gradient 0˜20% ethyl acetate-toluene
  14. customThe first peak collected from the column