Methanol → (2S,4R)-methyl 4-(allylthio)-4-(biphenyl-4-yl)pyrrolidine-2-carboxylate

HRID 2425797Notes

Reaction equation

HRID 2425797 reaction equation
[CH2:1]([S:4][C@:5]1([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[CH2:9][N:8](C(OCC2C=CC=CC=2)=[O:11])[C@H:7]([C:20]([O:22][CH3:23])=[O:21])[CH2:6]1)[CH:2]=[CH2:3].I[Si](C)(C)C.CO>C(#N)C>[OH2:11].[CH2:1]([S:4][C@:5]1([C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:28][CH:29]=2)[CH2:9][NH:8][C@H:7]([C:20]([O:22][CH3:23])=[O:21])[CH2:6]1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 57988337(2S,4R)-1-benzyl 2-methyl 4-(allylthio)-4-(biphenyl-4-yl)pyrrolidine-1,2-dicarboxylate

Product 2

HCID 962WaterHCID 57998023(2S,4R)-methyl 4-(allylthio)-4-(biphenyl-4-yl)pyrrolidine-2-carboxylateYield 49.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an iced solution of (2S,4R)-1-benzyl 2-methyl 4-(allylthio)-4-(biphenyl-4-yl)pyrrolidine-1,2-dicarboxylate (1.85 g, 3.79 mmol) in acetonitrile (20 mL) was added iodotrimethylsilane (0.810 mL, 5.69 mmol). The formed light brown solution was stirred at room temperature for 2 h. Cooled with ice bath, quenched with methyl alcohol (7.68 mL, 190 mmol). The formed light brown solution was purified by prep-HPL, and the collected fractions were evaporated on speed-vac system. The yellow residue was taken up in DCM, washed with sat. Na2CO3 and brine, dried over MgSO4, filtered, evaporated in vacuo to afford the desired product (2S,4R)-methyl 4-(allylthio)-4-(biphenyl-4-yl)pyrrolidine-2-carboxylate (664 mg, 1.878 mmol, 49.5% yield) as a viscous oil. 1H NMR (500 MHz, MeOD) δ ppm 2.93-3.08 (m, 3H) 3.11-3.20 (m, 1H) 3.77-3.88 (m, 1H) 3.92-3.99 (m, 3H) 4.04 (d, J=12.21 Hz, 1H) 4.72-4.80 (m, 1H) 5.02 (d, J=9.77 Hz, 1H) 5.09 (dd, J=16.94, 1.37 Hz, 1H) 5.54-5.70 (m, 1H) 7.35-7.42 (m, 1H) 7.43-7.56 (m, 4H) 7.60-7.68 (m, 2H) 7.69-7.77 (m, 2H). LC-MS (retention time; 2.21 min, method A), MS m/z 354 (M+H).

Workup

  1. temperatureCooled with ice bath
  2. customThe formed light brown solution was purified by prep-HPL, and the collected fractions
  3. customwere evaporated on speed-vac system
  4. washwashed with sat. Na2CO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ecbd5d417a7e416f8206460c5084f001
Source dataset
uspto-grants-2011_06
Patent number
US07964560B2

Reaction notes

Loading…